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Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
N-Metalated Imines as Intermediates for Pyrimidine and Cyclopentenone CompoundsLi
High yields in most cases
BLANGETTI, M.; DEAGOSTINO, A.; PRANDI, C.; ZAVATTARO, C.; VENTURELLO, P.
MVI
ArCNOEt
OEtLiC-KOR
Ar-CN OEt
MN Ar
PhCOCl
O
Ar NHCOPh
N
NAr Ar
OEt
M = Li, KAmberlyst-15
K
Chem. Commun. 1689 16912008 -, , 14 ,
Dianion Equivalent from Acylsilanes for Substituted ββββ-Keto Esters SynthesisLi
GALLIFORD, C. V.; SCHEIDT, K. A.
MVI
O
SiZ3R N2
Li CO2R1 OLi
Z3SiR
N2
CO2R1
OSiZ3
RCO2R1
Li
CZ3SiO
R OEt
OLi R2X
R3X
O
RCO2R1
R2 R3
Brook
-N2
Chem. Commun. 1926 19282008 -, , 16 ,
Disubstituted Pyridine SynthesesLi
VANDROMME, L.; REISSIG, H.-U.; GRÖPER, S.; RABE, J. P.
CC
NBr NAr RNAr Cl (or Br)
i) ArB(OH)2, K2CO3, Pd(PPh3)4, dioxane/H2O, reflux
ii) [nBuLi/LiDMAE], hexane then CBr4 or C2Cl6
RX, Mg, I2 (cat), Et2O,
Fe(acac)3, THF/NMP
BMgFe
Eur. J. Org. Chem. 2049 20552008 -, , 12 ,
Dynamic Behaviour of Arylallylic Lithium Compounds by X-Ray and NMRLi
FRAENKEL, G.; CHEN, X.; GALLUCCI, J.; REN, Y.
MVI
NO
O Li+
H
Transition state :
J. Am. Chem. Soc. 4140 41452008 130 -, , 12 ,
1
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Chiral Lithiated IntermediatesLi
HOGAN, A.-M. L;. O’SHEA, D. F.
CC
NHBn
R
R'NHBn
R
O O
NLi
R
R'
Li
Bn
N
R
(CH2)3OH
R'
Bn
MeOH
R = H, F, OMe R' = Et, nHex, nBu
20 examplesYields = 15-76% er 92:8
i) PhLi (1 eq), cumene, rt, 15 min.
ii) R'Li (2 eq), (-)-spartene (3 eq), -15°C, 4h
for example
i)
ii) HCl (aq)
J. Org. Chem. 2503 25092008 73 -, , 7 ,
Diastereoselective Metalated Nitrile AlkylationLi
FLEMING, F. F.; LIU, W.; GHOST, S.; STEWARD, O. W.
CC
R
CN CN
ERi) LDA (1.05 eq), THF, -78°C, 50 min.
ii) E+ (1.2 eq), THF, -78°C, 3h
R = Me, Ph Yields = 52 - 88%
Mg
J. Org. Chem. 2803 28102008 73 -, , 7 ,
Regio- and Stereoselective Lithiation of 2,3-DiphenylaziridinesLi
Multinuclear NMR investigation is reported.
CAPRIATI, V.; FLORIO, S.; LUISI, R.; MAZZANTI, A.; MUSIO, B.
CC
NPh
Ph
Pr
NPh
Li
Pr
Ph
NLi
LiNPh
Ph
Pr Ph
Ph
LL
L L
NPh
E
Pr
PhNPh
Pr
E
PhL = TMEDA
sBuLiTMEDA
toluene
sBuLi
THF
E+ E+
J. Org. Chem. 3197 32042008 73 -, , 8 ,
Synthesis of Trisubstituted AllenesLi
ZHAO, J.; LIU, Y.; MA, S.
CC
R
HAr
H R
R'Ar
H R' = aryl, alkenyl
R = nC5H11, nC6H13
Ar = Ph, Tol, pMeOC6H4
i) LDA (2 eq), -78°C to rt, 1hii) ZnBr2 (4 eq), rt, 20 min.
iii) Pd(PPh3)4 (5 mol%) R'I (0.8 eq), rt
16 Examples Yields = 56 - 92%
ZnPd
Org. Lett. 1521 15232008 10 -, , 8 ,
2
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Trans-1,4-DiphosphacyclohexaneLi
MORISAKI, Y.; IMOTO, H.; OUCHI, Y.; NAGATA, Y.; CHUJO, Y.
CC
PP
Me
MeRR
BH3
BH3
PP
RR
BH3
BH3
PP
RRP
PCH2Li
CH2LiRR
BH3
BH3
sBuLi, THF
(-)-sparteine
(S,S)-isomer trans trans
i) CuCl2
ii) NH3aq
-BH3
Org. Lett. 1489 14922008 10 -, , 7 ,
Asymmetric Deprotonation of N-Boc-PyrrolidineLi
STEAD, D.; O’BRIEN, P.; SANDERSON, A.
CC
N
Boc
N
N
tButBu
N
Boc
i) sBuLi (1.3 eq), Et2O, -78°C, 3h
ii) CuCN.2LiCl (0.5 eq), -78°C, 1hiii) CH2=CHCH2Br (1.8 eq), rt, 16h
(1.3 eq)
Yield = 78% er : 85/15
Org. Lett. 1409 14122008 10 -, , 7 ,
Diborylethyne SynthonLi
KANG, Y. K.; DERIA, P.; CARROLL, P. J.; THERIEN, M. J.
CC
Cl
Cl H
Cl
OB
OiPrO
BO
O
OB
OOR
RO
I
I
OR
RO n
i) nBuLi (3 eq), THF/Et2O, -78°C then 12h, rt
ii) Et2O/THF, 4h, -78°C then 2h, rtiii) anhydrous HCl, -78°C then rt Yield = 77%
(R = -(CH2)3SO3Na)
Pd(OAc)2 (1.5 mol%)/TPXTS1.5 M aq NaOH, µw,150°C, 90 min.
TXPTS = tris(4,6-dimethyl-3-sulfonatophenyl) phosphine trisodium salt
B
Org. Lett. 1341 13442008 10 -, , 7 ,
Stable Hypercarbon CB62- -Based Cluster-Assembled Complexes : CpM(CB6)
q-Li
YANG, L.-M.; HE, H.-P.; DING, Y.-H.; SUN, C.-C.
LS
B C BBB
BB
Computational study : a general strategy for designing stable hypercarbon CB62--based
cluster-assembled compounds CpM(CB6)q- (M = Li, Na, K, Be, Mg and Ca) is proposed. Various sandwich-type interactions are studied.
BNaKBeMgCa
Organometallics 1727 17352008 27 -, , 8 ,
3
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Electrophilic Trapping of Dilithio(hetero)arenes.Li
Sequential electrophilic trapping reactions are described leading to desymmetrization of dilithio(hetero)arenes.
MUSCHELKNAUTZ, C.; SAILER, M.; MÜLLER, T. J. J.
BP
Br-(hetero)arylene-Br E1-(hetero)arylene-E21) 2 equiv. n-BuLi (TMEDA), THF, -78 °C, 30 min.
2) Electrophile E1, -78 °C, 3 h3) Electrophile E2, -78 °C, 40 min.
8 examples, yields 39-63 %
Synlett 845 8482008 -, , 6 ,
s-BuLi/(-)-Sparteine-Mediated Chiral Deprotonation of a Piperazine.Li
MCDERMOTT, B. P.; CAMPBELL, A. D.; ERTAN, A.
BP
NNO
ONN
O
Os-BuLi, (-)-sparteineCO2, Et2O, -78 °C
HO2CHATU, DIPEADMF, 25 °C
NNO
O
ON
NBn
48 % over 2 steps, er = 89:11
Synlett 875 8792008 -, , 6 ,
Synthesis of 2,5-Disubstituted 3-(Methylsulfanyl)thiophenes.Li
FATTUONI, C.; USAI, M.; CADONI, E.; CABIDDU, M. G.; DE MONTIS, S.; CABIDDU, S.
BP
S
S CH3 1) BuLi (2.5 equiv.), THF, -78 °C
2) R1X3) R2X
S
S CH3
R1 R212 examples, yield : 25-69 %
Synthesis 985 9892008 -, , 6 ,
Synthesis of Sulfonyl Azides.Li
KATRITZKY, A.; WIDYAN, K.; GYANDA, K.
BP
R-M + SO2
Bt-Cl, Et3NR S
O
O
BtNaN3
MeCNR S
O
O
N3
Bt = Benzotriazol-1-yl
14 examplesYields 23-90 %
M = Li, MgCl, MgBr
Mg
Synthesis 1201 12042008 -, , 8 ,
4
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Lithiation of Acenaphthylene and Reaction with Carbonyl Compounds.Li
Lithiation of acenaphthylene catalyzed by 4,4’-di-tert-butylbiphenyl (DTBB).
LILLO, V. J.; GÓMEZ, C.; YUS, M.
BP
1) Li, DTBB (7.5 mol%), -70 °C
2) R1R2CO, -70 to -30 °C3) H2O, - 30 °C to r.t.
OH OHR1
R2R1
R2
OHR1
R2
60-84%1:0-1:12
9 examples
Synthesis 1241 12482008 -, , 8 ,
Polysubstituted PyrrolesLi
DAVIS, F. A.; BOWEN, K. A.; XU, H.; VELVADAPU, V.
CC
N
O
R Y
Boc
N
O
R Y
R'
Boc
N
OH
R Y
H
R'
Y = COOMe, P(O)(OMe)2
i) LDA (3 eq), THF, -78°C, 1h
ii) R'X (1.5 eq),THF, 2h
i) TFA
ii) SiO2, air
8 ExamplesYields = 40 - 88%
R = Ph, tBu, 2-furyl
Tetrahedron 4174 41822008 64 -, , 19 ,
Regioselective Reductive Opening of Non-Symmetrically Substituted PhthalansLi
GARCIA, D.; FOUBELO, F.; YUS, M.
CC
O
R
X
OHR
i) Li (10 eq), DTBB (5 mol%), -78°C or -78°C to -50°C, THF, 3h.
ii) E+, -78°Ciii) H2O, -78°C to rt
Numerous Examples Yields = 25 - 95%
R = H, Ph or OMe
Tetrahedron 4275 42862008 64 -, , 19 ,
1,2-Spiroannelated Five-Membered RingsLi
WIDJAJA, T.; FITJER, L.; MEINDL, K.; HERBST-IRMER, R.
CC
OOH
Li
OOH
i) CeCl3 (2 eq), THF, 2h, 0°C
ii) (1.25 eq), 30 min., rt
77%
Tetrahedron 4304 43122008 64 -, , 19 ,
5
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
One-Pot Oxidative C-C Bond FormationLi
MATSUO, J.-I.; TANAKI, Y.; ISHIBASHI, H.
CC
NH
R
H
N
R
NH
R
Nui) nBuLi (1.3 eq), THF, -78°C, 15 min.
ii) PhS(Cl)=NtBu (1.5 eq), THF, -78°C, 30 min.
Nu-H (1.6 eq), THF
-78°C, 30 min.
R = Ar, vinyl, CH=CHPh Yields = 36 - 84%
Tetrahedron 5262 52672008 64 -, , 22 ,
Alkyllithium - Lithium Methoxide Mixed AggregatesLi
Computational study is reported.
PRATT, L. M.; KWON, O.; CHI HO, T.; VAN NGUYEN, N.
CC
(R-Li)n + (RO-Li)n (R-Li)x (RO-Li)y
Tetrahedron 5314 53212008 64 -, , 22 ,
αααα-Substituted Monoalkyl- and DialkylbenzenediphosphonatesLi
TVERDOMED, S. N.; RÖSCHENTHALER, G.-V.; KALINOVICH, N.; LORK, E.; DOGADINA, A. V.; IONIN, B. I.
CC
(EtO)2P
(EtO)2P
CH3
R
O
O
(EtO)2P
(EtO)2P H
O
O
F
(EtO)2P
(EtO)2P CH3
O
O
F
OHi) LDA (2 eq), THF, -80°C, 30 min.
ii) for example E+ = pFC6H4CHO
R = H, CH3
for R = Hfor R = CH3
Yield = 45%Yield = 30%
or
Tetrahedron 5306 53132008 64 -, , 22 ,
γγγγ-Organoselenium and γγγγ-OrganotelluriumLi
OKORONKWO, A. E.; ROSARIO, A. R.; ALVES, D.; SAVEGNAGO, L.; NOGUEIRA, C. W.; ZENI, G.
CC
R H R YOH( )n
i) nBuLi (1 eq), THF, -78°C, 1h
ii) Y0 (1 eq) (0°C or 70°C)iii) Br(CH2)nOH (0.5 eq), rt
R = alkyl, aryl Y = Se, Ten = 2, 3, 6
Numerous examples Yields = 19 - 97%
SeTe
Tetrahedron Lett. 3252 32562008 49 -, , 20 ,
6
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Synthesis of 1,2-Aminoalcohols by [2,3]-Wittig RearrangementsLi
BARBAZANGES, M.; MEYER, C.; COSSY, J.
CC
R
NTs
OH
SiMe3
PhCH2
PhCH2
N
O
R
SiMe3Ts
LDA, THF, -78°C
R = Me, CH2OPMB
Yields = 76 - 87% dr = 9/1- 10/1
Tetrahedron Lett. 2902 29062008 49 -, , 18 ,
Addition of Ethyl Lithiodiazoacetate to AldehydesLi
LI, P.; MAJIRECK, M. M.; KORBOUH, I.; WEINREB, S. M.
CC
R
OH
N2
CO2Et
Li
N2 CO2Et R
O
N2
CO2Et
RCHOTHF, -78°C
Yields = 42 - 96%
DMP
CH2Cl2, rt
Tetrahedron Lett. 3162 31642008 49 -, , 19 ,
1-Alkynyl CyclopropanolLi
AN,Y.; LIU, J.; JIANG, H.-Y.; WANG, Y.; CHEN, Z.
CC
SO2PhOHR Li
OH
R
Yields = 44 - 90 % (2.0 eq),
THF, 2h, -30°C
Tetrahedron Lett. 3124 31282008 49 -, , 19 ,
Epoxides for Use in Lateral Metalation of Isoxazoles Li
NELSON, J. K.; BURNS, C. T.; SMITH, M. P.; TWAMLEY, B.; NATALE, N. R.
CC
O
R
LiN O
O N
CH3
CH3CH3
Tetrahedron Lett. 3078 30822008 49 -, , 19 ,
7
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Transmetallation Behaviour of [M(P4HR4)] Salts toward Rhodium(I) and Copper(I)Na
First targeted synthesis of a transition metal complex containing a tetraphosphanide anion
S. GOMEZ-RUIZ, R. WOLF, E. HEY-HAWKINS
CM
[Na2(THF)4(P4Mes4)]1/ HCl, 1 eq
2/ [{RhCl(COD)}2][Rh(P4HMes4)(cod)] [Rh2(µ-P2HMes2)(µ-PHMes)(cod)2]+
26% 16%
+ other unindentified products
(cod)Rh
P P
PP
MesHMes
MesMes
KRhCu
Dalton Trans 1982 19882008 -, , 15 ,
Efficient Synthesis of 1,3-Oxathiolane-2-thionesNa
This one-pot synthesis is promoted by catalytic sodium hydride and methanol.
YAVARI, I.; GHAZANFARPOUR-DARJANI, M.; HOSSAINI, Z.; SABBAGHAN, M.; HOSSEINI, N.
OS
O
Me HCS2
SO
Me H
S
MeOH+
NaH (10 mol%)96%
Synlett 889 8912008 -, , 6 ,
New Route to 1,2-Diamino-4,5-phthalodinitrile .Na
BURMESTER, C.; FAUST, R.
BP
NS
NNC
NC
NaBH4, EtOH
r.t., 24 h, 53 %
NC
NC
NH2
NH2
Br
Br
NH2
NH2
Synthesis 1179 11812008 -, , 8 ,
Synthesis of a Mixed Alkali Metal BorohydrideK
Tuning the decomposition temperature in complex hydrides; applications in hydrogen storage
E. A. NICKELS, M. OWEN JONES, W. I. F. DAVID, S. R. JOHNSON, R. L. LOWTON, M. SOMMARIVA, P. P. EDWARDS
CM
LiK(BH4)2 X-ray characterizationThermogravimetric studies
Li
Angew. Chem. Int. Ed. 2817 28192008 47 -, , 15 ,
8
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Selective ββββ-HydroxyethylationMg
Various substituted epoxides were coupled with modest to excellent yields, under these conditions.
SIEGMUND, A.; RETZ, D.; XI, N.; DOMINGUEZ, C.; BÜRLI, R.; LIU, L.
OS
NN
O
OH
O
BnOO
NH
N
OO
BnO
92%
CHCl3, 35 °C, 16 h.
Mg(ClO4)2 1 equiv.+
10 equiv.
Synlett 1005 10082008 -, , 7 ,
Triorganozincates Addition to N-(tert-butanesulfinyl)imines.Mg
Triorganozincates as nucleophiles for diastereoselective addition to N-(tert-butanesulfinyl)imines.
ALMANSA, R.; GUIJARRO, D.; YUS, M.
BP
Ph H
NS
But
O
Ph R(R')
HNS
But
O
1) RMgBr-R'2Zn (1.5 equiv.)
2) NH4Cl (aq.)
dr up to 98:2, 14 examples, yields 28-99 %R, R' = Me, Et, n-C5H11, iPr, vinyl
Zn
Tetrahedron Asymm. 603 6062008 19 -, , 5 ,
Constrained Geometry Rare-Earth Metal Complexes: Synthesis and Catalytic Application.Sc
Mechanistic studies are presented. Catalytic activity increases with metal ionic radius.
ZHANG, W. X.; NISHIURA, M.; MASHIKO, T.; HOU, Z.
GR
LnSiN
Ar
NMe2
(THF)n
Ar= 2,4,6-Me3C6H2Ln= Y, La, Pr, Nd, Sm, Gd, Lu : n=1)Ln= Sc: n= 0
catalytic application: PH
R2
R1 N
C
N
R3
R4
+ P C
R2
R1 N
HN R4
R3
13 examples
YLaPrNdSmGd
Chem. Eur. J. 2167 21792008 14 -, , 7 ,
Bis(Oxazolinyl)Pyridine Scandium Complexes for Asymmetric Diels–Alder Reactions.Sc
Electron-withdrawing Pybox substituents give rise to higher enantioselectivity.
WANG, H.; WANG, H.; LIU, P.; YANG, H.; XIAO, J.; LI, C.
GR
O
NRO
O+
cat.R
O N O
O
R=H, Me
NO
N N
O
Sc(OTf)3
X
R' R'
cat:R'= iPr, Ph, tBu, Bn
X= H, Cl, Br, OMe, NMe2
ee up to 96%
J. Mol. Catal. A 128 1312008 285 -, , 1 ,
9
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Anilido-Phosphinimine Dimethyl Scandium Complexes.Sc
Various C-H bond activation processes are observed, upon thermal treatment or under hydrogen atmosphere.
CONROY, K.D.; PIERS, W. E.; PARVEZ, M.
GR
PR2
N NAr
Li
ScCl3(THF)3 PR2
N NAr
Sc
MeLi
Cl Cl
PR2
N NAr
Sc
Me Me
J. Organomet. Chem. 834 8462008 693 -, , 5 ,
Isoprene Polymerization with Yttrium Amidinate Catalysts.Y
Change in selectivity upon AlMe3 addition is explained by the formation of heterobimetallic Y/Al species.
ZHANG, L.; NISHIURA, M.; YUKI, M.; LUO, Y.; HOU, Z.
GR
N
Y
N
Ph
ArAr
R R
Ar: 2,6-iPr2C6H3
R: CH2(o-C6H4NMe2)
cat:[CPh3][B(C6F5)3]
cat. / AlMe3 (>3eq)
n
1,4-cis-PI > 98%
[CPh3][B(C6F5)3]
cat.
n
iso-3,4-PI > 99%
Al
Angew. Chem. Int. Ed. 2642 26452008 47 -, , 14 ,
New Chiral Lanthanide Amide Ate Complexes for Intramolecular Hydroamination.Y
The countercation nature is shown to exert an influence on the system peformances (Li>K).
AILLAUD, I.; COLLIN, J.; DUHAYON, C.; GUILLOT, R.; LYUBOV, D.; SCHULZ, E.; TRIFONOV, A.
GR
N
NLn
R
R
N
N
R
R
[M(THF)n]
Ln= Yb: R= c-C6H11, c-C5H9, CH2tBu, iPrLn= Y: R= c-C5H9, iPrM= Li, K
NH2
nRR cat.
RR
NHn cat:
9 substratesee up to 87%
YbLiK
Chem. Eur. J. 2189 22002008 14 -, , 7 ,
Zeolite NaY-Promoted Cyclisation of FarnesalY
TSANGARAKIS, C.; LYKAKIS, I. N.; STRATAKIS, M.
LS
Me
MeMe
O
Me
HMe
Me
Me
CHOMe Me
O
MeMe
NaY
70°C, 3h+
1a (d.r. = 92/8)1b(E)/1c(Z)
1a/1b/1c = 5/4/182% yield
J. Org. Chem. 2905 29082008 73 -, , 7 ,
10
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Synthesis of 4-Alkoxy-2-aryl-1,2,3,4-tetrahydro-quinoline DerivativesCe
10 examples, yields: 67-77%; imino Diels-Alder (Povarov) reaction.
SRIDHARAN, V.; AVENDANO, C.; MENENDEZ, J.C.
GJ
NH2
CHO OEt
NH
H
H
OEt(NH
4)2Ce(NO
3)6
+ +
72%
(5 mol%)
MeCN, rt, 45 min
Synthesis 1039 10442008 -, , 7 ,
Construction of Cyclopenta[b]benzofuran Skeleton Involving Reductive CouplingSm
A route to racemic rocaglamide and its 2,3-di-epi analogue is described.
LI, H.; FU, B.; WANG, M. A.; LI, N.; LIU, W. J. ; XIE, Z. Q. ; MA, Y. Q.; QIN, Z.
OC
O
O
OMe
OMe
MeO O
OMe
MeO
OH CONMe2
HO
OMe
O
OMe
MeO
OH CONMe2
HO
OMe
+
1. PhCH=C(COOMe)22. SmI2, us
3. Me2NLi, −78 °C4. Me4NBH(OAc)3
Eur. J. Org. Chem. 1753 17582008 -, , 10 ,
Reaction of Ketenes with Lanthanocene Amide and Imidazolate Complexes.Yb
Crystal structures of the complexes have been determined.
LIU, R.; ZHENG, P.; WENG, L.; ZHOU, X.; LIU, C.
GR
C OPh
Ph
[Cp2Ln(C3H3N2)]2 NN LnCp2
O
Ph
Ph
N NCp2Ln
O
Ph
Ph
[Cp2Ln(NHnBu)]2Cp2Ln
ON
nBuPh
Ph
LnCp2
ON
nBuPh
PhH
H
ErDy
J. Organomet. Chem. 1614 16202008 693 -, , 8-9,
Bridgeg Half-sandwich Titanium ComplexesTi
XIAO T.; WANG J.; ZHANG Y.; GAO W.; MU Y.
GN
Synthesis, structures and catalytic properties for ethylene polymerization of bridgeg titanium complexes.
OTMS
R2
R1
TMS
Ph H
O
R2R1
PhH
TiCl
Cl
TiCl4
J. Organomet. Chem. 1195 12022008 693 -, , 7 ,
11
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Titanium Tetraisocyanide ComplexesTi
ALLEN J.M.; ELLIS J.E.
GN
Reaction of the Ti(0) carbonyl anion [CpTi(CO) 4]- with I 2, Ph3SnCl, and Me 3SnCl in the presence of four equivalents of CNXyl, where Xyl = 2,6-dimethylpheny l, affords titanium tetraisocyanides complexes, [CpTi(CNXyl) 4E], E = I, SnPh 3, SnMe3, which have been characterized by IR and NMR spect roscopy and single-crystal X-ray crystallography.
Sn
J. Organomet. Chem. 1536 15422008 693 -, , 8-9,
Synthesis of Homoallyl Ethers and ChloridesTi
MERISOR, E.; CONRAD, J.; MALAKAR, C. C.; BEIFUSS, U.
BJL
ROH + HC(OMe)3
Lewis acid
RX X: Cl or OMe
InBiB
Synlett 903 9072008 -, , 6 ,
Enantioselective Hetero-Diels-AlderTi
LI, X.; MENG, X.; SU, H.; WU, X.; XU, D.
BJL
OMe
Me3SiO
+ RCHO
1. Ti-L* additive
2. CF3CO2H
O
O R
43-99%, 11-84% ee
L*:OHN
OH
Synlett 857 8602008 -, , 6 ,
Chemioselective Oxidation of Secondary AlcoholsTi
SHEI, C.T.; CHIEN, H. L.; SUNG, K.
BJL
R1 R2
OH
R1 R2
OTiCl4/TBHP (0.1:1.7)
60-85%
Synlett 1021 10262008 -, , 7 ,
12
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Ti(IV) Reductive AminationTi
SALMI, C.; LONCLE, C.; LETOURNEUX, Y.; BRUNEL, J. M.
CC
R R'
O
OHNH2
R R'
NHOH
+i) Ti(OiPr)4 (1.3 eq), MeOH, rt, 5-6h
ii) NaBH4 (1 eq), 0°C, 2h then rt, 20 min.(3 eq)
10 ExamplesYields = 11 - 89%
Tetrahedron 4453 44592008 64 -, , 19 ,
Synthesis of Optical Activity Analysis of Chiral Titanium(IV)Ti
Asymmetric methylation of benzaldehyde was studied with chiral group IV sec-butoxides.
MACMILLAN, S. N.; LUDFORD, K. T.; TANSKI, J. M.
TJ
MN
N
N
N
M = Ti, Zr, Hf
OH
*M
O
O
O
O
*
*
*
*
+C6H6
example:Ti(OR-2Bu)4:
[α]D = -83.1 10-1degcm2g-1
ZrHf
Tetrahedron Asymm. 543 5482008 19 -, , 5 ,
Regio- and Stereoselective Preparation of Dienylcarboxylic AcidsTi
OGATA, A.; NEMOTO, M.; TAKANO, Y.; TSUBOUCHI, A.; TAKEDA, T.
TJ
R1
SO2Me
FG
R2
+R1 FG
R21. Cp2Ti[P(OEt)3]2
2. H2O
FG = CO2Li, PO(OEt)2
R1 = Ph, C6H13, CH2CH2PhR2 = CH3, C6H13, CH2CH2Ph
14 examples59-86%
2E > 91%
Tetrahedron Lett. 3071 30742008 49 -, , 19 ,
Interconversion of Zirconaaziridine EnantiomersZr
Kinetic measurements
CUMMINGS, S. A.; TUNGE, J. A.; NORTON, J. R.
BPH
NCp2Zr
R2
R1N
Cp2Zr
R2
R1
OO
O
Ph Ph OCp2Zr
NR1
R2
OO Ph
Ph
k1
k2
J. Am. Chem. Soc. 4669 46792008 130 -, , 14 ,
13
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Catalytic Asymmetric Alkylations of KetoiminesZr
R1 = Ar, Alk, R2 = CO2Me, CF3
FU, P.; SNAPPER, M. L.; HOVEYDA, A. H.
BPH
R1 R2
N
MeO
Chiral ligand (0.1 equiv)Zr(Oi-Pr)4, i-PrOH (0.1 equiv)
Me2Zn (4 equiv)toluene, 22 °C, 48 h
R1 R2
HN
MeO
Me
79-97% ee
chiral ligand :
t-Bu
OHt-Bu
NH
i-Pr
O BnNHBu
O
J. Am. Chem. Soc. 5530 55412008 130 -, , 16 ,
Formal SN2’ SubstitutionZr
Scope and mechanism detailed
LALIC, G.; KRINSKY, J. L.; BERGMAN, R. G.
BPH
OR+
N-TBS
OCp2Zr
R1R2
1) C6D6, 23 °C
2) Cbz-Cl
NHCBz
R2
R1
76-99%
In similar conditions : E isomers : <20% yield
J. Am. Chem. Soc. 4459 44652008 130 -, , 13 ,
Linear Triene FormationZr
Also three examples of tetraenes !
KANNO, K.; IGARASHI, E.; ZHOU, L.; NAKAJIMA, K.; TAKAHASHI, T.
BPH
R1 R1
+R2 R2 Cp2ZrCl2
2 EtMgBrCp2Zr
R1
R1
R2R2
1) NCS
2) R3 R3
CuCl, 0 °C3) H+
R3R1
Cl
R3R1
R2 R2
R1 = Alk, R2 = Ar, R3 = CO2R32-64% (isolated)
Cu
J. Am. Chem. Soc. 5624 56252008 130 -, , 17 ,
(Amidomethyl)pyridine Zirconium and Hafnium Complex esZr
NIENKEMPER K.; KEHR G.; KEHR S.; FROHLICH R.; ERKER G.
GN
NR2
HN
R1
Ar
R3
NR2
N
R1
Ar
R3
(NMe2)3Hf
Hf(NMe2)4Zr(NMe2)4NR2
N
R1
Ar
R3
(NMe2)3Zr
Substituted N-arylaminoalkylpyridine derivatives we re synthesized and used as ligands for (chelate ligand) MX3 systems (M = Zr,Hf). Some of these gave very active ethene polymerization catalysts.
Hf
J. Organomet. Chem. 1572 15892008 693 -, , 8-9,
14
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Synthesis and Reduction Behavior of Novel Sandwich Complexes of ZirconiumZr
BELOV S.A.; KIRSANOV R.S.; KRUT’KO D.P.; LEMENOVSKII D.A.; CHURAKOV A.V.; HOWARD J.A.K.
GN
ZrCl
Cl
N(CH3)2
Me3Si
Me3Si ZrH
Me3Si
Me3SiNCH3
Mg/Hg, THF
20°C, 5 days
J. Organomet. Chem. 1912 19182008 693 -, , 10 ,
Detailed Mechanisms on Insertion of cis-2-butene into Zr-H Bond of Cp2ZrH 2Zr
BI S.; KONG X.; ZHAO Y.; ZHAO X.; XIE Q.
GN
Cp2*Zr
H
H
Cp2*Zr
H
+
The mechanisms for both the side-insertion and the central-insertion of cis-2-butene into the Zr-H bond of Cp2ZrH2 to give Cp2Zr(H)(CH2CH2CH2CH3) were explored with the aid of DFT calculations.
J. Organomet. Chem. 2052 20602008 693 -, , 11 ,
Use of ZrO(OTf)2 as Catalyst for Trimethylsilylation of Alcohols with HMDSZr
MOGHADAM M.; TANGESTANINEJAD S.; MIRKHANI V.; MOHAMMADPOOR-BALTORK I.; CHAHARDAHCHERIC S.;TAVAKOLI Z.
GN
2 R-OH + Me3SiNHSiMe3
ZrO(OTf)2
ACN2 R-OSiMe3 + NH3
Rapid and efficient trimethylsilylation of alcohols and phenols with hexamethyldisilazane catalyzed by reusable zirconyl triflate [ZrO(OTf)2] is reported. Primary, secondary and tertiary alcohols as well as phenols were efficiently converted to their corresponding TMS ethers.
J. Organomet. Chem. 2041 20462008 693 -, , 11 ,
Reactions of MCl4(PMe3)2 Complexes (M = Hf, Nb) with Cyclohexadienyl AnionHf
HARVEY B.G.; BASTA R.; ARIF A.M.; ERNST R.D.
GN
Nb PMe3Hf PMe3
Nb
J. Organomet. Chem. 1420 14252008 693 -, , 8-9,
15
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Oxidative Coupling of 2-NaphtholsV
TAKIZAWA, S.; KATAYAMA, T.; KAMEYAMA, C.; ONITSUKA, K.; SUZUKI, T.; YANAGIDA, T.; KAWAI, T.; SASAI, H.
GJ
OH
OH
OHO
N
V OO
O
N
VOO
O O OHOH
CH2Cl2, 0°C,
72 h
catalyst (5 mol%), air
catalyst
Chem. Commun. 1810 18122008 -, , 15 ,
Cyclopentadienyl-Silyl-Amido and Imido Niobium Complexes. Nb
Reaction outcome depends on the amine nature; DFT calculations have been performed to support experimental results.
MAESTRE, M. C.; MOSQUERA, M. E. G.; JACOBSEN, H.; JIMÉNEZ, G.;CUENCA, T.
GR
MCl ClCl
Cl
SiMe2ClR-NH2
MClClCl
SiMe2Cl
MCl NCl
SiMe2Cl
N
R
R
Organometallics 839 8492008 27 -, , 5 ,
Agostic Distortions in Early-Transition-Metal Alkyl Complexes.Nb
DFT studies are presented.
PANTAZIS, D. A.; MCGRADY, J. E.; BESORA, M.; MASERAS, F.; ETIENNE, M.
GR
[Nb]
HC
H3C
CH2
Me
Ph
H [Nb]
CH3C
CH3
Me
Ph
H
vs. [Nb]= [HB(Me2pyr)3]NbCl
β-agostic interaction α-agostic interaction
Organometallics 1128 11342008 27 -, , 6 ,
Unexpected Formation of (Dimethylaminomethylene)Methylamide Complexes.Nb
No definitive mechanism for the formation of the amido-amine ligand could be proposed.
ZHANG, X.-H.; CHEN, S.-J.; CAI, H.; IM, H.-J.; CHEN, T.; YU, X.; CHEN, X.; LIN, Z.; WU, Y.-D.; XUE, Z.-L.
GR
MCl5 + 5 LiNMe2 M(NMe2)5 + MMe2N
Me2N NMe2
NMe2
NMe2
MeNM= Nb, Ta
Ta
Organometallics 1338 13412008 27 -, , 6 ,
16
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Zwitterionic Niobium and Tantalum Imido Complexes.Nb
Theoretical and methyl methacrylate polymerization studies are presented.
ARTEAGA-MÜLLER, R.; SÁNCHEZ-NIEVES, J.; RAMOS, J.; ROYO, P.; MOSQUERA, M. E. G.
GR
MCl3(NR)(Py)2
MCl2(NR)(OAr)(Py)2
LiOAr
BnMgCl
BnMgClN
M
R
Ph
PhPh
N
MO
R
Ph
ArPh
THF
E(C6F5)3
E(C6F5)3
2 eq.
M = Nb, TaR = tBu, 2,6-iPr2C6H3Ar = 2,6-iPr2C6H3E= B, Al
N
M
R
Ph
Ph E(C6F5)3
N
MO
R
Ph
Ar E(C6F5)3-(THF)E(C6F5)3
TaZr
Organometallics 1417 14262008 27 -, , 7 ,
Non-Oxidative Coupling Reaction of Methane to Ethane and Hydrogen.Ta
Catalysis by a silica-supported tantalum hydride.
SOULIVONG, D.; NORSIC, S.; TAOUFIK, M.; COPÉRET, C.; THIVOLLE-CAZAT, J.; CHAKKA, S.; BASSET, J.-M.
BP
2 CH4> 250 °Ccat.,
C2H6 + H2 cat. :
Si
O
Si
OTa
H
J. Am. Chem. Soc. 5044 50452008 130 -, , 15 ,
Linear Ta-H-B Geometry. Ta
Crystal structure of the complex shows an essentially linear Ta–H–B interaction.
HILL, A. F.; SMITH, M. K.; WAGLER, J.
GR
TaCl Cl
Cl
Cl+ 2 B
H HSS
Na
BH H
SS BNNN N
S SH H
Na
=TaCl
B
H
H SHHSNa
V IV
Organometallics 2137 21402008 27 -, , 9 ,
[8+2] and [8+3] Cyclisations of Alkenyl CarbenesCr
BARLUENGA, J.; GRACIA-RODRIGUEZ, J.; MARTINEZ, S.; SUAREZ-SOBRINO, A. L.; TOMAS, MIGUEL
PG
NOMe[M]
R'
R
+
NR
H
R'
CO2Me
[M] = Cr(CO)5or W(CO)5
7 examples79-91%
NR
O
HR'[8+2] [8+3]
9 examples21-85%
W
Chem. Asian J. 767 7752008 3 -, , 4 ,
17
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Carbene Complexes: Enantiopure Aminocarbenes of CrCr
MECA, L.; CISAROVA, I.; GRAHONOVSKY, D.; DVORAK, D.
RE
MeO2C
CH3 Cr(CO)5
NMé2
(S)-1-(1-naphthyl) ethanol
O2C
CH3 Cr(CO)5
NMé2
MeO2C
CH3 Cr(CO)5
NMé2
1) crystalisation2) MeOH
Organometallics 1850 18582008 27 -, , 8 ,
Selective cis-Dihydroxylation of OlefinsMo
Recyclable homogeneous molybdenum acetylide catalyst
A. V. BIRADAR, B. R. SATHE B, S. B. UMBARKAR, M. K. DONGARE
CM
R R' R R'
OHHOCpMo(CO)3(C CPh)H2O2
tBuOH, 65°Cconv: 45-92%
J. Mol. Catal. A 111 1192008 285 -, , 1-2,
Tungsten Allyl Complexes and AminesW
[W] = WCp*, Cp* = C5Me5
TSANG, J.Y.K.; BUSCHHAUS, M.S.A.; FUJITA-TAKAYAMA, C.; PATRICK, B.O.; LEGDZINS, P.
RF
[W] CH2tBu
ON
NH
N
[W] CH2tBu
NO
- H2
Organometallics 1634 16442008 27 -, , 7 ,
Directed Formation of Allene Complexes .Mn
Formation of a 1:1 mixture of syn/anti isomers, each characterized by X-ray analysis.
SENTETS, S.; SERRES, R.; ORTIN, Y.; LUGAN, N.; LAVIGNE, G.
HJR
Mn
OC
Tol
PhCO
Mn
OC CO
1) LiPCy2, / THF, -80°C2) CF3SO3H / THF, -80°C-r.t.
H
PCy2Ph
Tol
Brown crystals, 55%
Mn
OC CO Ph
Tol H
PCy2
+
Yellow crystals, 26%
O
Organometallics 2078 20912008 27 -, , 9 ,
18
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Supported Pyrazole Rhenium ComplexesRe
Catalysts for cyclohexane oxidation with O2
G. S. MISHRA, E. C. B. ALEGRIA, L. M. D. R. S. MARTINS, J. J. R. FRAUSTO DA SILVA, A. J. L. POMBEIRO
CM
O OH
+
[ReClxFy{N2C(O)Ph}(pyrazole)z(PPh3)k]
immobilized on 3-aminopropyl functionalized silica
O2
no solvent, no additive
overall conversion = 16% max
J. Mol. Catal. A 92 1002008 285 -, , 1-2,
Reduction of 2,2'-Bipyrimidine in the Self-Assembly of Metal-Based Rectangles.Re
Partially reduced ligand unambiguously characterized by 1H NMR and X-ray analysis.
WU, J.-Y.; THANASEKARAN, P.; CHENG, Y.-W.; LEE, C.-C.; MANIMARAN, B.; RAJENDRAN, T.; LIAO, R.-T.; LEE, G.-H.;PENG, S.-M.; LU, K.-L.
HJR
N
N
N
N+ Re2(CO)10+ pyrazine
Re
CO
CO
OC
NN
NN
Re
CO
OC
OC
Re
CO
CO
NN
NN
Re
COOC
N-L-N
N-L-N CO
CO
N-L-N = pyrazine
Purple crystals, 67%
C4H9OH, 160 °C, 48 h
Organometallics 2141 21442008 27 -, , 9 ,
Ferrocenyl Complexes: in vitro Biological Effect Against Breast CancerFe
HEILMANN, J.B.; HILLARD, E.A.; PLAMONT, M.-A.; PIGEON, P.; BOLTE, M.; JAOUEN, G.; VESSIERES, A.
RE
Fe
RR
J. Organomet. Chem. 1716 17222008 693 -, , 8,9,
Ferric-Chloride-catalyzed Reductive Halogenation of Carbonyl Compounds.Fe
Synthesis of bromides and iodides from keto compounds.
LI, Z.; SHENG, C.; YANG, C.; QIU, H.
CB
R
O
R'MeCl2SiH
(1.5 equiv)
+5% FeCl3
PBr3 (1.1 equiv)
NaI (1.5 equiv)
R
Br
R'
R
I
R'
CH3CN
reflux / 4-10h
reflux / 6-24h
42-97%
71-95%
Org. Prep. Proc. Int. 608 6112007 39 -, , 6 ,
19
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Synthesis of αααα-Oxo ThiocyanatesFe
15 examples, yields: 68-84%.
YADAV, J.S.; REDDY, B.V.S.; REDDY, U.V.S.; CHARY, D.N.
GJ
O OFeCl
3SCN
CH2Cl2, rt, 40 min
78%
Synthesis 1283 12872008 -, , 8 ,
Characterization of Intermediates Relevant to Ring Closing Metathesis Catalysis.Ru
Spectroscopic characterization of ruthenacyclobutane and ruthenium olefin carbene intermediates are given.
VAN DER EIDE, E. F.; ROMERO, P. E.; PIERS, W. E.
BP
N NMesMes
RuCl
ClCH
PR3 A
N NMesMes
RuClCl
C
CC
H
HH CO2Me
CO2Me
α
βαH
J. Am. Chem. Soc. 4485 44912008 130 -, , 13 ,
Ru-Cat Dienyne Synthesis from 1,3-Dienes and Propargylic Alcohols Ru
DAINI, M.; YOSHIKAWA, M.; INADA, Y.; UEMURA, S.
PG
Ar
OH
R
R
Ar
R
R
+ Ru Ru
S
SCl
*Cp
iPr
iPr
Cp*
Cl
Ru-Cat (5 mol %)NH4BF4 (10 mol %)
ClCH2CH2Cl60°C, 1 h
7 examples67-80%
Ru-Cat :
Organometallics 2046 20512008 27 -, , 9 ,
New Highly Active Bimetallic Precatalyst for Alkene Metathesis Ru
VINOKUROV, N.; GARABATOS-PERERA J. R.; ZHAO-KARGER, Z.; WIEBCKE, M.; BUTENSCHÖN, H.
PG
NMesMesN
Ru
OiPr Cr(CO)3
ClCl
Organometallics 1878 18862008 27 -, , 8 ,
20
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Triosmium and Triruthenium Carbonyl ClustersOs
Activation of two C-H bonds of NHC N-methyl groups.
J. A. CABEZA, I. DEL R¾O, D. MIGUEL, E. PEREZ-CARRENOC, M. G. SANCHEZ-VEGA
CM
Os Os
Os
N
N
CH3
CH3= CO
Toluene, 110°C
5hOs Os
Os
NNCH3C
H
H H
Ru
Dalton Trans 1937 19422008 -, , 14 ,
Hydride Complexes of Osmium and RutheniumOs
Preparation of chelate vinyl derivatives by reaction with propargylic alcohols
G. ALBERTIN, S. ANTONIUTTI, A. BACCHI, G. PELIZZI, G. ZANARDO
CM
P
Os
PCP
P OP
Os
PCP
PC
HH
H
R
Ph
+
C
O C
H
H
H
R
Ph+
+HC CCPh(R)OH
OsH(κ1-OTf)P4
Ru
Eur. J. Inorg. Chem. 1913 19202008 -, , 11 ,
Triosmium and -Ruthenium ClustersOs
LI C.; LEONG W.K.
GN
Os Os
OsOH
HOs Os
OsE
H
Os Os
OsE
H
OsOs
OsE'
H
The reaction of triosmium and -ruthenium clusters with bifunctional ligands carrying -OH, -SH and -COOH groups is described. The structure of eight of the compounds obtained have also been determined.
+ E'HHE
E'H
+
Ru
J. Organomet. Chem. 1292 13002008 693 -, , 7 ,
Osmium Carbyne ComplexesOs
LEE J-H.; PINK M.; SMURNYY Y.D.; CAULTON K.G.
GN
The mechanism of conversion of terminal alkynes RCCH to coordinated carbyne OsCCH2R by Os(H)2ClXL2 (L =
PiPr3) has been studied for X = OTf and B(ArF)4 (ArF = 3,5-di(CF3)2(C6H3). The energy of various intermediates,
including the only experimentally unobserved one, η2-vinyl, was evaluated with DFT(PBE) calculations.
Os
L
L
CH2R
XCl
HOs(H)2ClL2X + RCCH
X = OTf or BAr4
B
J. Organomet. Chem. 1426 14382008 693 -, , 8-9,
21
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
New Triosmium-iridium ClustersOs
Synthesis and molecular structure of new osmium-iridium mixed-metal clusters
LEE Y-B.; WONG W-T.
GN
OsOH
Os
Os
Ir
COCO
COOC
CO
Ir
OC
OC
OC
CO
ClOC OsOH
Os
Os
Ir
COCO
COOC
ClOC
OC
OC
CO
COOC
Ir
J. Organomet. Chem. 1528 15352008 693 -, , 8-9,
Pauson-Khand Reactions with Tricobalt Carbonyl ClustersCo
good yields but low enantiomeric excess
MOBERG, V.; MOTTALIB, M. A.; SAUER, D.; POPLAVSKAYA, Y.; CRAIG, D. C.; COLBRAN, S. B.; DEEMING, A. J.;NORDLANDER, E.
MVI
EtOOCEtOOC
CO OEtOOCEtOOC P P
[Co3(µ3-CH)(CO)7(R,R-DuPhos) *
R,R-DuPhos
Dalton Trans 2442 24532008 -, , 18 ,
Cyclotrimerisation of Phenylacetylene with Co Catalysts Containing Disulfide LigandsCo
HILT, G.; HENGST, C.; HESS, W.
OC
Ph
3
Ph
Ph Ph Ph
Ph
PhCo(ligand)Br2
Zn, ZnI225 °C, < 30 min
S S PhPh
NN cHexcHex
ligand: 2.9 : 1
1 : 19.2
96 % in CH2Cl2
99 % in CH3CN
+
Eur. J. Org. Chem. 2293 22972008 -, , 13 ,
Co-Catalyzed Hydrolytic Kinetic Resolution (HKR) of EpoxidesCo
RAJ, I. V. P.; SUDALAI, A.
CC
O
R
O
RYields = 46-47% ee = 94-98%
(R,R)- or (S,S)-Co(III)salen.OAc (0.5 mol%),
H2O (0.55 eq), rt
R = Ph or pMeOC6H4
Tetrahedron Lett. 2646 26482008 49 -, , 16 ,
22
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Styrene Hydroformylation.Rh
Influence of the position and lenght of the R group on the selectivity.
GUO, Y.; FU, H.; CHEN, H.; LI, X
MJ
CHO
CHO
Rh(acac)(CO)2 (cat.)
CO/H2 (1:1, 1.5 Mpa)
PhMe, 50 °C
MeO P
R
R
(2eq./Rh)
+
Catal. Commun. 1842 18452008 9 -, , 9 ,
Asymmetric Hydroformylation of meso-Bicyclic HydrazinesRh
BOURNAUD, C.; LECOURT, T.; MICOUIN L.; MÉLIET, C.; AGBOSSOU-NIEDERCORN, F.
OC
NCOR
NCOR
NCOR
NCORHO
1. Rh(acac)(CO)2 (1 mol%) L* (2 mol %) H2/CO (1:1) Toluene
2. NaBH4 MeOH
up to 77.5 % ee
N
PPh2
Ph2P
Boc
L*:
(S,S)-BPPM
Eur. J. Org. Chem. 2298 23022008 -, , 13 ,
Catalytic Rhodium Nitrene/Alkyne MetathesisRh
THOMTON, A. R.; BLAKEY, S. B.
PJF
OSO2NH2
BnO
O
NHS
O
OBn
O O
Rh2(esp)2, PhI(OAc)2
Then NaBH4, MeOH
71%
J. Am. Chem. Soc. 5020 50212008 130 -, , 15 ,
Mechanism of Rhodium Catalyzed Aldehydes DecarbonylationRh
Kinetic studies and DFT calculations
FRISTRUP, P.; KREIS, M.; PALMELUND, A.; NORRBY, P.-O.; MADSEN, R.
PJF
O RhCl (5 mol%), dppp
diglyme, Reflux
J. Am. Chem. Soc. 5206 52152008 130 -, , 15 ,
23
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
New Abnormal N-Heterocyclic Carbene Rhodium and Iridium ComplexesRh
M = Ir, Rh
SONG, G.; ZHANG, Y.; LI, X.
PJF
MCl
N
N
R
Organometallics 1936 19432008 27 -, , 8 ,
Base Free C=X ReductionIr
CORBERAN, R.; PERIS, E.
PJF
O
N
N
Ir
nBu
nBu
X
X ClCl
OH
iPrOH
Organometallics 1954 19582008 27 -, , 8 ,
Asymmetric Ni-Catalyzed Conjugate Allylation of Activated EnonesNi
The mechanism is discussed
SIEBER, J. D.; MORKEN, J. P.
MVI
O
Ar pentyl
B(pin)O
Ar pentylP
O
O
O
O
Ar Ar
Ar Ar
Ph5 mol% Ni(cod)2
1.5 equiv
toluene, rt91-94% ee10 mol% L
Ar = 3,5-di-t-butylphenyl
J. Am. Chem. Soc. 4978 49832008 130 -, , 14 ,
Ni-Catalyzed Addition of C-H Bonds of Terminal Alkynes to 1,3-Dienes and StyrenesNi
The regiochemistry is discussed
SHIRAKURA, M.; SUGINOME, M.
MVI
PhSiiPr3 Ph
SiiPr3
Ni(cod)2 (1-10 mol%)PBu3 (P/N = 4)
toluene, rt96%
J. Am. Chem. Soc. 5410 54112008 130 -, , 16 ,
24
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Ni/NHC-Catalyzed CycloadditionsNi
Cycloadditions of diynes and carbonyl reagents are reported ; mechanisms are proposed.
TEKAVEC, T. N.; LOUIE, J.
CC
O
R
R'
( )n
R
( )n O
R
R"R'
( )n
n = 1,2
Ni(cod)2 (10 mol%),
IPr (15 mol%),toluene, rt, R'COR"
Ni(cod)2 (5 mol%),
SIPr (10 mol%),toluene, rt, R'CHO
Yields = 67-97% Yields = 77-98%
J. Org. Chem. 2641 26482008 73 -, , 7 ,
Ni-Catalyzed AllylationNi
SUMIDA, Y.; HAYASHI, S.; HIRANO, K.; YORIMITSU, H.; OSHIMA, K.
CC
OBocR
R"
ROH
R'R'
R"
R"
R+
Ni(cod)2 (5 mol%),P(OEt)3 (10 mol%),
toluene, reflux, 5h
(1.2 eq)
+
Org. Lett. 1629 16322008 10 -, , 8 ,
Synthesis of Methyl 7-Oxo-1-oxa-6-azaspiro[4.4]nonane-8-carboxylatesNi
10 examples.
SUKHORUKOV, A.YU.; LESIV, A.V.; KHOMUTOVA, Y.A.; IOFFE, S.L.; NELYUBINA, Y.V.
GJ
ON
CH3
CH3
CO2Me
CO2Me
CH3
NO
O
H
CH3
CH3
CH3
CO2Me
NO
O
H
CH3
CH3
CH3
CO2Me
NO
O
H
CH3
CH3
CH3
CO2Me
NO
O
H
CH3
CH3
CH3
CO2Me
+ + +
Raney NiMeOH
H2 (70 bar)
80°C, 2 h
77% (5.4:1.1:4.1:1.0)
Synthesis 1205 12202008 -, , 8 ,
Ni-Catalyzed Carbonylative Negishi Coupling ReactionsNi
WANG, Q.; CHEN, C.
CC
N N
OMeMeO
R
R
R
R
O
1
2
3
4RX
R
R
1
2
3
X = OTf or I
+ R42Zn
CO (1 atm), NiCl2-L (2-5 mol%)
MgBr2 (1.8 eq), DMSO 23-80°C, 20-40 min.
L =
(1.3 eq) Yields = 72 - 95%
Zn
Tetrahedron Lett. 2916 29212008 49 -, , 18 ,
25
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Pd-Catalyzed Asymmetric TMM [3+2] Cycloaddition: a HighlightPd
Phosphoramidite ligands (L*) are excellent chirality transfer agents in these reactions.
LE MARQUAND, P.; TAM, W.
CY
OAcTMS RR
*+
Pd cat., L*
[3+2]
(TMM = trimethylenemethane)
Angew. Chem. Int. Ed. 2926 29282008 47 -, , 16 ,
Iterative C–H Bonds Functionalization for the Total Synthesis of AlkaloidsPd
BECK, E. M.; HATLEY, R.; GAUNT, M. J.
CY
NBoc
TMS
HN
N
Et
O
OC–H Pd-cat. alkenylation
C–H Ir-cat. borylation,then Suzuki
rhazinicine
Ir
Angew. Chem. Int. Ed. 3004 30072008 47 -, , 16 ,
Ambitious sp2–sp3 Suzuki Cross-CouplingPd
PATERSON, I.; ANDERSON, E. A.; DALBY, S. M.; LIM, J. H.; GENOVINO, J.; MALTAS, P.; MOESSNER, C.
CY
OO
OMeO
TESOCl
TBSO
I
PMBOOH
OMe
a) 9-BBN, THF; H2O;
b)
PdCl2(dppf), Ph3As,Cs2CO3, THF/DMF (1:1)
OO
OMeO
TESOCl
TBSO
PMBOOH
OMe
Angew. Chem. Int. Ed. 3016 30202008 47 -, , 16 ,
Aryl Ketones Decarboxylative Cross-CouplingPd
GOOΒEN, L. J.; RUDOLPHI, F.; OPPEL, C.; RODRIGUEZ, N.
CY
O
O
OK
OMe
Br+
CuBr (15 mol%), Pd(F6-acac)2 (1 mol%),1,10-phenanthroline (15 mol%),P(o-Tol)3 (2 mol%), NMP/quinoline (3:1)
O
OMe83%
Cu
Angew. Chem. Int. Ed. 3043 30452008 47 -, , 16 ,
26
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Hydroarylation of Alkenes with Boronic EstersPd
IWAI, Y.; GLIGORICH, K. M.; SIGMAN, M. S.
CY
B
F
O
O
[Pd(SiPr)Cl2]2 (0.75 mol%),(–)-sparteine (6 mol%),
tBuOK (6 mol%), iPrOH,O2, 55 ºC, 24 h
+
F
78%
SiPr =NN
iPr
iPr Pri
Pri
Angew. Chem. Int. Ed. 3219 32222008 47 -, , 17 ,
Pd-Catalyzed Hydrogen Transfer Semireduction of AlkynesPd
Good to excellent chemo- and stereoselectivities are obained.
HAUWERT, P.; MAESTRI, G.; SPRENGERS, J. W.; CATELLANI, M.; ELSEVIER, C. J.
CY
R1 R2
R1 R2
Cat. (1 mol%),HCO2H/NEt3 (5 equiv),THF or MeCN, reflux Cat. =
N
NPd
O
O
O
solvent
Angew. Chem. Int. Ed. 3223 32262008 47 -, , 17 ,
Dissolution and Redistribution of Pd over a Pd Foil Used as CatalystPd
Re-deposition of Pd take place at the cool edges of the locally heated reaction zone of the Pd foil in the above modelcross-coupling reaction.MACQUARRIE, S.; HORTON, J. H.; BARNES, J.; MCELENEY, K.; LOOCK, H.-P.; CRUDDEN, C. M.
CY
BO
OO2N I+
Pd foiliPr2NEt, DMF
localized heatingO2N
Angew. Chem. Int. Ed. 3279 32822008 47 -, , 17 ,
Hiyama Cross-Ccoupling Reaction.Pd
Lower yield with NaOH instead of TBAF. No reaction with CsF or KF.
PAN, C.; LIU, M.; ZHAO, L.; WU, H.; DING, J.; CHENG, J.
MJ
Ar1X + Ar2Si(OMe)3PdCl2 (0.05 eq.)
TBAF.3 H2O (1 eq.)PhMe, 100 °C, 10 h
(2 eq.)Ar1-Ar2 X = Br: 80-96%
X = Cl:31-77%
Si
Catal. Commun. 1685 16872008 9 -, , 8 ,
27
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Pd-Catalyzed Intramolecular Diamination of AlkenesPd
MUNIZ, K.; HOVELMANN, C. H.; CAMPOS-GOMEZ, E.; BARLUENGA, J.; GONZALES, J. M.; STREUFF, J.; NIEGER, M.
PG
NH
NHTosO
N N Tos
O
RR R
R
Pd(OAc)2 (10 mol %)CuBr2 (3 equiv)K2CO3 (1equiv)
DMF, 40°C
R'
R'
5 examples75-99%
Cu
Chem. Asian J. 776 7882008 3 -, , 4 ,
Reduction of CeriaPd
ACERBI, N.; TSANG, S. C; GOLUNSKI, S. COLLIER, P.
BJL
CeO2 (ceria) is widely used as a catalysts support. The combination of platinum group metals (PGM) with ceria is known to lower the ceria reduction temperature. The authors have been able to demonstrate a direct correlationbetween PGM promotion of the ceria surface and the work function of the metal. An electronic interaction plays acrucial role in the metal-ceria interface.
PtRhRuAg
Chem. Commun. 1578 15802008 -, , 13 ,
Three-Component Coupling of Arynes, Allylic Compound and Terminal AlkynesPd
BHUVANESWARI, S.; JEGANMOHAN, M.; YANG, M.-C.; CHENG, C.-H.
BJL
OTfR1
R2 SiMe3
+ X
R3
R4
R5+ R6
Pd(PPh3)4, CuI
CsF
R1
R2
R3
R4R5
R669-92%
Chem. Commun. 2158 21602008 -, , 18 ,
Pd-domino Sequence for Tricyclic HeterocyclesPd
HU, Y.; SONG, F.; WU, F.; CHENG, D.; WANG, S.
MF
N
O
Br N
O
R
R
Pd(OAc)2 2% / PPh3 4%
nBu3, DMF , 155 °C
R = EWG, EDG
22 Examples
Chem. Eur. J. 3110 31172008 14 -, , 10 ,
28
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Pd Nanoparticles Supported on Siliceous Mesocellular Foam for Heterogeneous CatalysisPd
ERATHODIYIL, N.; OOI, S.; SEAYAD, A. M.; HAN, Y.; LEE, S. S.; YING, J. Y.
MF
MCF
OH
OH
OH
HO MCF
OH
OH
HO
HNO
NHR Pd(MeO)3Si
HN
O
NHRPd(OAc)2
Toluene, 60 °C
MCF : Siliceous MesoCellular FoamSuzuki at 80 °CHeck at 100 °C
Hydrogenation at r.t.Reductive Amination at r.t.
ReusableCatalyst
Chem. Eur. J. 3118 31252008 14 -, , 10 ,
Enantioselective Addition of Arylboronic Acids to Cyclic Enones Mediated by NHC-PdPd
ZHANG, T.; SHI, M.
MF
N
N
N
N
PdO
O
O
O
CR3
CR3
Me
Me
R = H, F
O O
ArArB(OH)2
NHC-Pd
KOH, H2O/THF, r.t.
3 %mol
NHC-Pd
Chem. Eur. J. 3759 37642008 14 -, , 12 ,
Pd-catalyzed Three-Components Coupling for Synthesis of DiarylketonesPd
NEUMANN, H.; BRENNFÜHRER, A.; BELLER, M.
MF
Br (HO)2BR1 R2 R1
O
R2COPd(OAc)2 / L P nBu
2.5-10 bars TMEDA, Toluene80-120 °C
L :
Chem. Eur. J. 3645 36522008 14 -, , 12 ,
Phosphite–Oxazoline/Oxazine Ligand for Allylic SubstitutionPd
DIÉGUEZ, M.; PÀMIES, O.
MF
ON O
P
OO
R
R
R
R
RR R
X
R R
Nu
Nu H
Pd/L Cat.
Ligand
Chem. Eur. J. 3653 36692008 14 -, , 12 ,
29
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
4-(1',3'-Dien-2'-yl)-2,5-dihydrofuran Synthesis from AllenolsPd
DENG, Y.; LI, J.; MA, S.
MF
. R
HOR1
.OH
O
R
R1
PdI2
BF3. Et2ODMSO, 80 °C
Chem. Eur. J. 4263 42662008 14 -, , 14 ,
Homeopathic Catalysts Loading for Suzuki Coupling in WaterPd
FLECKENSTEIN, C. A.; PLENIO, H.
MF
+HP Cy
Cy
SO3H
SO3H
HSO4-
Hydrosoluble Ligand
Na2PdCl4 / LClHeteroAryl
Ar B(OH)2
ArHeteroAryl
0.01-0.05 mol %
100 °C, K 2CO3H2O
Chem. Eur. J. 4267 42792008 14 -, , 14 ,
Contrasting Bonding Modes of a Tridentate Bis(oxazoline)phosphine Ligand Pd
Unprecedented eight-membered ring chelates.
KERMAGORET, A.; BRAUNSTEIN, P.
BS
N
OP
N
O
PhCoFe
Dalton Trans 585 5872008 -, , 5 ,
Pd(II) Complexes with Mixed Benzothiazolin-2-ylidene and Phosphine LigandsPd
Moderate to good catalytic activity in Suzuki-Miyaura coupling reaction of aryl bromides and chlorides.
YEN, S. K.; KOH, L. L.; HUYNH, H. V.; HOR, T. S. A.
BS
Novel Pd(II) mixed N,S-heterocyclic carbene (NSHC)-phosphine complexes
Dalton Trans 699 7062008 -, , 5 ,
30
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Pd-catalysed Asymmetric Mono- and Bis-alkoxycarbonylation of VinylarenesPd
GODARD, C.; MUÑOZ, B. K.; RUIZ, A.; CLAVER, C.
BS
Ph+ CO + MeOH
O
OMe
*
Ph
Ph O
OMe
O OMe
*Ph OMe
O
[Pd]/LOxidant
[Pd]/L'L'bidentate
[Pd]/L'L monodentate
Dalton Trans 853 8602008 -, , 7 ,
Pd-cat. Aminations of Aryl Halides with Phosphine-functionalized Imidazolium LigandsPd
SHI, J.-C.; YANG, P.; TONG, Q.; JIA, L.
BS
RX + NR1R2
RNR1R2
Pd(OAc)2/L (0.001 - 0.02 eq.)
L = PPh2
N
NR3Fe
I
Dalton Trans 938 9452008 -, , 7 ,
Cross-Coupling Reactions of Triorganoindium Reagents with Alkenyl HalidesPd
RIVEIROS, R.; SAYA, L.; SESTELO, J. P.; SARANDESES, L. A.
BJL
R1 Br
Br
1. R23In
Pd (cat)
2. R33In
Pd (cat)
R1 R2
R3
50-99%
Eur. J. Org. Chem. 1959 19662008 -, , 11 ,
Synthesis of 2,6-Disubstituted PyridinesPd
The sequence involves Suzuki coupling, ortholithiation/halogenation and Negishi coupling
VANDROMME, L.; REIßIG,H.-U.; SUSIE GRÖPER, S.; RABE, J. P.
BJL
NBr
1. ArB(OH)2, K2CO3
Pd(PPh3)4 (cat)
2. n-BuLi-LiDMAE, C2Cl6
3. Fe(acac)3 (cat), RMgBr NAr R
Fe
Eur. J. Org. Chem. 2049 20552008 -, , 12 ,
31
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Aqueous C–C CouplingPd
The immobilized palladium catalyst is leach proof and recyclable
TSVELIKHOVSKY, D.; BLUM, J.
BJL
X
R + Reagents C-C coupling[Pd] cat.
K2CO3
Microemulsion
[Pd]: Pd(OAc)2 entrapped within a hydrophobicitized silica sol–gel matrix
Reagents:R
, ArB(OH)2, PhSnBu3
Ph Ph / PhB(OH)2
BSn
Eur. J. Org. Chem. 2417 24222008 -, , 14 ,
Direct Arylation of EnaminonesPd
GE, H.; NIPHAKIS, M. J.; GEORG, G. I.
CJM
N
O
+ ArBF3K
Pd(OAc)2 30%Cu(OAc)2 3 EqK2CO3 2 Eq.
tBuOH AcOH DMSO60 °C
N
OAr 19 examples
up to 97% yield
J. Am. Chem. Soc. 3708 37092008 130 -, , 12 ,
Porphyrin ComplexesPd
MATANO, Y.; MATSUMOTO, K.; NAKAO, Y.; UNO, H.; SAKAKI, S.; IMAHORI, H.
CJM
N
NN
N
Ar
Ar P
Ar
M
Zn
N
NN
N
Ar
Ar
Zn
PhPh
PPhPh
Ar
M= Pd, Pt
PtZn
J. Am. Chem. Soc. 4588 45892008 130 -, , 14 ,
Catalyst Poisoning in the Cyanation of Aryl HalidesPd
ERHARDT, S.; GRUSHIN, V. V.; KILPATRICK, A. H.; MACGREGOR, S. A.; MARSHALL, W. J.; ROE, D. C.
CJMJ. Am. Chem. Soc. 4828 48292008 130 -, , 14 ,
32
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
C-C Triple Bond CleavagePd
WANG, A.; JIANG, H.
CJM
R2R1 + R3OH R1COOR3 + R2COOR3
Pd(OAc)2 2%ZnCl2•2H2O 20%
O2 7.5 Atm.R3OH (solvent) 100 °C
J. Am. Chem. Soc. 5030 50312008 130 -, , 15 ,
Arylallenes via a Retropropargylation of Homopropargyl AlcoholsPd
HAYASHI, S.; HIRANO, K.; YORIMITSU, H.; OSHIMA, K.
CJM
ROH+ ArBr
Pd2dba3 2.5%PnOct3 20%Dimethylacetamide 70%KOH 2 equiv.
Toluene, reflux H
• R
Ar
H
J. Am. Chem. Soc. 5048 50492008 130 -, , 15 ,
Enantioselective Intramolecular Heck-Iminium CyclizationPd
Total synthesis of Minfiensine
DOUNAY, A. B.; HUMPHREYS, P. G.; OVERMAN, L. E.; WROBLESKI, A. D.
CJM
NOTf CO2Me
BocHN Pd(OAc)2 L*pentamethylpiperidine
toluene, 100 °C75-85% yield, 89% ee
NCO2Me
BocHN
TFA
NCO2Me
NBoc
J. Am. Chem. Soc. 5368 53772008 130 -, , 15 ,
5-exo-dig Hydroarylation of AlkynesPd
CHERNYAK, N.; GEVORGYAN, V.
CJM
R1
R2 Pd(OAc)2 5%NHC 7%
Toluene, 120°C
R1
R2
18 examples47-98% yield
J. Am. Chem. Soc. 5636 56372008 130 -, , 17 ,
33
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Hydroperoxide Formation: MechanismPd
KONNICK, M. M.; STAHL, S. S.
CJM
NHC
PdBzO H
NHC
- BzOH
Slow(NHC)2Pd0
O2, BzOH
Fast
NHC
PdBzO OOH
NHC
J. Am. Chem. Soc. 5753 57622008 130 -, , 17 ,
Autocatalytic Oxidative AdditionPd
Oxidative addition is faster with Pd(II) than with Pd(0)
BARRIOS-LANDEROS, F.; CARROW, B. P.; HARTWIG, J. F.
CJM
Ph-Br(PtBu3)2Pd0
slow
(PtBu3)2PdII(H)Br
fast(PtBu3)Pd(Br)Ph(PtBu3)Pd(Br)Ph
J. Am. Chem. Soc. 5842 58432008 130 -, , 18 ,
Palladium-Catalyzed Hydrostannation of Substituted Propargyl Alcohols.Pd
FARAONI, M. B.; GERBINO, D. C.; PODESTA, J. C.
AM
R
R1HOR2
R
Nph3Sn
R1HO
R2
syn α
RR1
HOR2
syn β
+
SnNph3
Nph3SnH+PdCl2(PPh3)2
THF
Nph = Neophyl = CH2CM2PhR, R1, R2 = H, alkyl, Rh
Sn
J. Organomet. Chem. 1877 18852008 693 -, , 10 ,
Hydrogenation.Pd
Influence of the amount of Pd/C on the selectivity.
LI, X.; MENG, X.; SU, H.; WU, X.; XU, D.
MJ
NH2
OH
(S)
5% Pd/C
H2 (80 bar)EtOH, 80 °C, 10 h
NH2
OH
NH2
OH+
18-33% 48-66%
Synlett 857 8602008 -, , 6 ,
34
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Cross-Couplings.Pd
Synthesis of the Se/Te starting materials described.
ALVES, D.; PRIGOL, M.; NOGUEIRA, C. W.; ZENI, G.
MJ
Se Ph
TeBu
Ph Pd(PPh3)4 (0.15 eq.)Ag2O, NEt3
MeOH, reflux, 24 h
71%Pd(acac)2 (0.1 eq.)CuI (0.2 eq.), NEt3MeOH, reflux, 4 h
BF3KPhMeO BF3K
Se PhPh
Se PhPh
PhOMe
68%
AgCuBTeSe
Synlett 914 9182008 -, , 6 ,
Addition to N-Tosylarylimines.Pd
28 examples. Ligand, catalyst, solvent and base screening.
ZHANG, Q.; CHEN, J.; LIU, M.; WU, H.; CHENG, J.; QIN, C.; SU, W.; DING, J.
MJ
N
Ts
Ph
+ PhB(OH)2(2 eq.)
PdCl2(PhCN)2 (0.05 eq.)i-Pr2NPPh2 (0.05 eq.)
K2CO3 (3 eq.), MS 4Ådioxane, 80 °C, 24 h 83%
NH
Ts
Ph
Ph
B
Synlett 935 9392008 -, , 6 ,
Heck Reaction.Pd
Use of these compounds to carry out [3+3] cyclizations.
MROΒ G.; REINKE, H.; LANGER, P.
MJ
Cl
O
EtO
R1
R3
R2
Pd(OAc)2 (0.01 eq.)NEt3 (1.2 eq.)
(4 eq.)
+80 °C, 24 h
6 examples, 32-54%
O
R1
R3
R2
EtO
Synlett 963 9662008 -, , 7 ,
Intramolecular Heck Reaction, 9-endo-trig Cyclization.Pd
6 examples.
MAJUMDAR, K. C.; CHATTOPADHYAY, B.
MJ
MeN
NMe
O
BrO
O
MeN
NMeO
OO
90%
Pd(OAc)2 (0.1 eq.)n-Bu4NBr (1.2 eq.)KOAc (2.75 eq.)
DMF, 100 °C, 2-3.5 h
Synlett 979 9822008 -, , 7 ,
35
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Intramolecular Oxidative Coupling.Pd
Various conditions tested. Also from furan derivatives.
BECCALLI, E. M.; BORSINI, E.; BROGGINI, G.; RIGAMONTI, M.; SOTTOCORNOLA, S.
MJ
S N
CO2Et
PdCl2(MeCN)2 (0.15 eq.)CuCl2 (0.15 eq.)
O2, DMF, 100 °C, 2 h
70%
S N
CO2Et
Cu
Synlett 1053 10572008 -, , 7 ,
Tandem [2+1]Cycloaddition-Ring Expansion.Pd
7 examples.
BIGEAULT, J.; DE RIGGI, I.; GIMBERT, Y.; GIORDANO, L.; BUONO, G.
MJ
OAc+
(2 eq.)
Pd(OAc)2 (0.05 eq.)CyPhP(O)H (0.1 eq.)
PhMe, 60 °C60%
OAc
Synlett 1071 10752008 -, , 7 ,
Pd-Cat Synthesis of 3-Indoles Carboxylic Acid DerivativesPd
SÖRDERBERG, B. C. G.; BANINI, S. R.; TURNER, M. R.; MINTER, A. R.; ARRINGTON, A. K.
PG
NO2
CO2R'
RNH
CO2R'
R
Pd(dba)2 (10 mol %)dppp (15 mol %)
1,10--phenatroline (30 mol %)
CO (6 atm), 120°C
10 examples 74-95%
Synthesis 903 9122008 -, , 6 ,
Chiral Phosphoramidites Ligand for Pd-Cat Asymmetric Hydrosilylation of StyrenesPd
LI, X.; SONG, J.; XU, D.; KONG, L.
PG
OO
P
Cl
OMe
SiCl3
R R
HSiCl3 (2 equiv)[Pd(C3H5)Cl]2 (0,125 mol %)
Ligand* (0,5 mol %)
rt, neat
9 examples65-96% yield - 73-97% ee
Ligand* :
Synthesis 925 9312008 -, , 6 ,
36
Bibliographic Notebooks For Organometallic Chemistry2008, 26, ( 4)
Pd-Cat Synthesis of Conjugated Dienes Pd
LEMHADRI, M.; BATTACE, A.; BERTHIOL, F.; ZAIR, T.; DOUCET, H.; SANTELLI, M.
PG
Ph2P PPh2Ph2PPPh2
Br
R''R'
R R'''[Pd(C3H5)Cl]2 (0,5 equiv)
Tedicyp (1 equiv)+
R''R'
R
R'''
Major isomer22 examples
TON up to 66 000
Tedicyp :
Synthesis 1142 11522008 -, , 7 ,
Application of Suzuki Cross-Coupling: Synthesis of Substituted Imidazoles.Pd
PRIMAS, N.; MAHATSEKAKE, C.; BOUILLO, A.; LANCELOT, J-C.; OLIVEIRA SANTOS, J. S.; LOHIER, J-F.; RAULT, S.
AM
N
NH
N
NB
O
O
NH
NAr
1) Suzuki cross-coupling reaction
2) Deprotection
4 steps
THP
B
Tetrahedron 4596 46012008 64 -, , 20 ,
Application of Palladium-Catalyzed Carbonylation.Pd
Formal synthesis of (+)-bakkenolide A using the title reaction is reported.
KATO, K.; MOTODATE, S.; TAKAISHI, S; KUSAKABE, T.; AKITA, H.
AM
R1
OH
O
+-
L* (7.5 mol %)Pd(TFA)2 (5 mol %)
p.benzoquinoneR2OH, CO balloon
O
R1R2O
OCO2R2DMP
oxidation21-23%92-97% ee
45-49%37-46% ee
+R1 = Me, Propyl, allyl
O
R1
OCO2R2
ON N
O
PhL*:
Ph
Tetrahedron 4627 46362008 64 -, , 20 ,
Pd-N-heterocyclic Carbene: Application in Carbon-Carbon Coupling Reaction.Pd
POLSHITTIWAR, V.; VARMA, R.S.
AM
X
R
R Y
R
YHeck reaction
organic Pd-NHC silica
DMF, MW
NNPd
N NII
Si
Si
OOO
OOO
OOO
OOO
R = H, Me, OMe, CHO, COMe, Fe, Cl, thiopheneX = Br, IY = CO2CH3, C6H5
[Pd] :
Tetrahedron 4637 46432008 64 -, , 20 ,
37
Bibliographic Notebooks For Organometallic Chemistry2008, 26, ( 4)
Palladium-Catalyzed Alkynes Oxidation.Pd
DMSO-PdI2 as powerful oxidizing couple of alkynes into benzils is reported.
MOUSSET, C., PROVOT, O.; HAMZE, A.; BIGNON, J.; BRION, J-P.; ALAMI, M.
AM
N
N Ar
Ar1Ar Ar1R
PdI2 (2 mol%)
DMSO, 140 °CAr
Ar1O
O
PdI2 (2 mol%)
DMSO, 140 °CNH2
NH2R
Tetrahedron 4287 42942008 64 -, , 19 ,
Palladium-Catalyzed Synthesis of Haloethynyl and Dihalovinyl Analogues of AZT and FLT.Pd
Synthesis and anti-HIV activity of AZT and FLT analogues are described.
JOUBER, N.; AMBLARD, F.; RAPP, K. L.; SCHINAZI, R. F.; AGROFOGLIO, L. A.
AM
O
OH
HO N
NH
O
OO
F/N3
HO N
NH
O
OO
F/N3
HO N
NH
O
O
II
Pd(0) I
X
and/or X = Cl, Br, I
Tetrahedron 4444 44522008 64 -, , 19 ,
Application of Suzuki Cross-Coupling Reaction in Synthesis of Ent-narciclasine.Pd
MATVENKO, M.; BANWELL, M. G.; WILLIS, A. C.
AM
O
O
B
OMOMCO2Me
OO OMOM
NH2
OMOM
OMOMBr+
NHO
O
OR
OOR
OR
OR
Pd(0), base
µ waveTMS-Br
R = MOMR = H
Tetrahedron 4817 48262008 64 -, , 21 ,
A Study of Heck Cyclization Reaction to Form Phenanthridine Ring Systems.Pd
DONALDSON, L. R.; HAIGH, D.; HULME, A. N.
AM
N PN P N P
HH
HH
Br
Hermann-Beller cat.Ag2CO3, DMF, ∆, <2h
P = SO2Me, BocCbz, Bn
Hermann-Beller cat.MeNCy2, MeCN, ∆, <5h
or Pd2(dba)3/tBu3PHBF4
MeNCy2, MeCN, <50°C
Ag
Tetrahedron 4468 44772008 64 -, , 19 ,
38
Bibliographic Notebooks For Organometallic Chemistry2008, 26, ( 4)
Selective C3-Arylation of Free NH-IndolesPd
CUSATI, G.; DJAKOVITCH, L.
TJ
NR1
H NR1
H
R2
R1 = H, Ph, CH3
+ Br R2K2CO3 3 equiv.
1 mol% [Pd(NH3)4]2+/NaYdioxane, reflux
24-48 h 18-95% conversions15-85% isolated yields
R2 = H, Cl, OCH3
CH3, NO2
Tetrahedron Lett. 2499 25022008 49 -, , 16 ,
Synthesis of 1,2-DihydroisoquinolinesPd
NAKAMURA, H.; SAITO, H.; NANJO, M.
TJ
NR2
R1
N
R1
R2
CCl3
2.5 mol % [Pd]5 mol% dppe
CHCl3, 100 °C
R1 = n-Bu, Ph, Cy2NCH2
R2 = Ar, Bn, n-Pr
12 examples32-99%
Tetrahedron Lett. 2697 27002008 49 -, , 17 ,
Regioselective Heck ArylationPd
LIU, Z.; XU, D.; TANG, W.; XU, L.; MO, J.; XIAO, J.
TJ
X
R RNHAc
3 mol% Pd(OAc)26 mol% DPPP
Et3N 2 equiv.[H2NiPr2][BF4] 4 equiv.
isopropanol, reflux
13 examples32-93%
+ NHAc
Tetrahedron Lett. 2756 27602008 49 -, , 17 ,
Direct C-H Activation/Functionalisation Reaction of HeteroaromaticsPd
GOTTUMUKKALA, A. L.; DERRIDJ, F.; DJEBBAR, S.; DOUCET, H.
TJ
O
N
or SO
N
or SR1
R3R2
5 mol % PdCl(C3H5)(dppb)
DMF, Cs2CO380-140 °C
BrR1
R3R2
+ 11 examples27-69%
Tetrahedron Lett. 2926 29302008 49 -, , 18 ,
39
Bibliographic Notebooks For Organometallic Chemistry2008, 26, ( 4)
Synthesis of 2,3-Dihydro-1H-pyrrolo[3,2-c]quinolinesPd
TOMASZEWSKI, M. J.; WHALLEY, A.; HU, Y.-J.
TJ
X
NH2
R4
R3
R2
R1
R4
R3
R2
R1N
N
OO
CHO
N
OO
+Pd(PPh3)4, K2CO3
Dioxane, microwave1 h, 170 °C
13 examples14-74%
X = I, Br
Tetrahedron Lett. 3172 31752008 49 -, , 19 ,
Synthesis of 4,6-Substituted CoumarinsPd
FERNANDES, T. A.; CARVALHO, R. C. C.; GONÇALVES, T. M. D.; DA SILVA, A. J. M.; COSTA, P. R. R.
TJ
R1
OHI
+ RCO2Et
O O
R1
R
H2O, Et3N, PdCl2
E or ZR1 = Cl, NO2,CO2Et
OOR = Me,
or Pd(OAc)270 °C, 40 h 6 examples, 44-90%
Tetrahedron Lett. 3322 33252008 49 -, , 20 ,
Pd-Catalyzed Indolization of 2-BromoanilinesPd
CUI, X.; LI, J.; FU, Y.; LIU, L.; GUO, Q.-X.
TJ
R1Br
NHR
+N
Rs
RL R
Rs
RL
Pd(OAc)2 1 mol%Phenylurea 4 mol%
K2CO3, DMF130 °C, 30 h
R1
14 examples55-86%
R = H, Me, AcR1 = H, Me
Rs, RL = Alkyl, Ar
Tetrahedron Lett. 3458 34622008 49 -, , 21 ,
A PCP-Pincer Liganded Anionic Platinum(0) ComplexPt
SCHWARTSBURD, L.; COHEN, R.; KONSTANTINOVSKI, L.; MILSTEIN, D.
CY
Pt
PtBu2
PtBu2
ClNa, THF
Pt
PtBu2
PtBu2
– Na+
Angew. Chem. Int. Ed. 3603 36062008 47 -, , 19 ,
40
Bibliographic Notebooks For Organometallic Chemistry2008, 26, ( 4)
Chemoselective Hydrogenation of ChloronitrobenzenePt
WANG, F.; LIUAB, J.; XU, X.
BJL
NO2
Cl
+ H2
[Pt] cat.[Pt]: Pt supported on Ag/γ-Zr(PO4)(NH4HPO4)
H2
NH2
Clselectivity 100%, up to 26000 TON
Chem. Commun. 2040 20422008 -, , 17 ,
Platinated-Copper Complexes as DNA Cleaving and Cytotoxics AgentsPt
OZALP-YAMAN, S.; DE HOOG, P.; AMADEI, G.; PITIÉ, M.; GAMEZ, P.; DEWELLE, J.; MIJATOVIC, T.; MEUNIER, B.;KISS, R.; REEDIJK, J.
MF
N NO
O
NNN
NNO
O
NN N
Pt
Cl
Cl
CuCl2 CuCl2H H
HH
Cu
Chem. Eur. J. 3418 34262008 14 -, , 11 ,
Tandem Intramolecular Hydroalkoxylation–Hydroarylat ion ReactionsPt
BARLUENGA, J.; FERNÁNDEZ, A.; SATRÚSTEGUI, A.; DIÉGUEZ, A.; RODRÍGUEZ, F.; FAÑANÁS, F. J.
MF
OH O O
R1 R1 R1
R2 R2 R2
Hydroalkoxylation Hydroarylation
AuI or PtII or PtIV
Au
Chem. Eur. J. 4153 41562008 14 -, , 14 ,
Reactivity of Pt- and Pd-bound Nitriles Towards Nitrile Oxides and NitronesPt
KUZNETSOV, M. L.; KUKUSHKIN, V. Y.; POMBEIRO, A. J. L.
BS
O
NN
R'
R
M
2
O
NCH3N
R'
R
M
2
R'C N-O
N CR)2M
R'C N-O M2
M O-NCHR'
CH3 2
M = Pd, Pt; [M] = trans-[MCl2]
Pd
Dalton Trans 1312 13222008 -, , 10 ,
41
Bibliographic Notebooks For Organometallic Chemistry2008, 26, ( 4)
Pt(II) Schiff Base as Versatile Phosphorescent Core ComponentPt
TONG, W.-L.; LAI, L.-M.; CHAN, M. C. W.
BS
OHC
OC7H14
C7H14O
OC7H14
C7H14O
O
N NH
CHO
C7H14O
OC7H14
C7H14O
OC7H14
O
OC7H14H14O7
Pt
Dalton Trans 1412 14142008 -, , 11 ,
Rational Design of Platinum(II) and Gold(III) Compl exes as Antitumour AgentsPt
WANG, X.; GUO, Z.
BS
Au
Dalton Trans 1521 15322008 -, , 12 ,
Azobenzene DiborationPt
BRAUNSCHWEIG, H.; KUPFER, T.
CJM
FeB
B
NMe2
NMe2
+N
N
Ph
Ph
Pt(PEt3)3 5%
Toluene 120 °C
FeB
B
NMe2
NMe2
NN
Ph
Ph
FeB
J. Am. Chem. Soc. 4242 42432008 130 -, , 13 ,
Cycloisomerization.Pt
5 examples.
KATO, K.; KOBAYASHI, T.; FUJINAMI, T.; MOTODATE, S.; KUSAKABE, T.; MOCHIDA, T.; AKITA, H.
MJ
Ph(CH2)2
AcO
1) Cat. (0.05 eq.)PhMe, rt, 48 h
2) Na2CO3 MeOH
O
(CH2)2Ph
Cat = AuCl3 (43%), PtCl4 (49%)
Au
Synlett 1081 10852008 -, , 7 ,
42
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Cu-Cat Three-Component Coupling Reaction: 2-Functionnalization of PyrroleCu
CHO, S. H. CHANG, S.
PG
17 examples, 54-91% yield
R
R' SO2N3
NH
R''
HN
R''R
NSO2R'
RN•
LnCu
SO2R'
NR''CuCl (10 mol %)
Et3N (1.2 equiv)
CHCl325°C, 2 h
Angew. Chem. Int. Ed. 2836 28392008 47 -, , 15 ,
Asymmetric Cu-Cat Propargylic AminationCu
DETZ, R. J.; DELVILLE, M. M. E.; HIEMSTRA, H.; VAN MAARSEVEEN, J H.
PG
R
OAc
+ ArNH2R
HNArCuI (10 mol %)
Ligand* (12 mol %)DIPEA (4 equiv)
MeOH, -20°C
14 examples62-97% yield / 13-87% ee
N
OO
N
Ph Ph
Ligand*
Angew. Chem. Int. Ed. 3777 37802008 47 -, , 20 ,
Cu-Catalyzed Domino Four-Component Coupling and Cyclization ReactionCu
OHTA, Y.; OISHI, S.; FUJII, N.; OHNO, H.
MD
+
CHO
(HCHO)nR2NH
then t-BoNH2
CuI (10 mol%)
DMF N
NR2
10 examples60-88% yield
Chem. Commun. 835 8372008 -, , 7 ,
Bio-Inspired Dicopper Catalyst Complex for Selective Benzylic C-C CouplingCu
PROKOFIEVA, A.; PRIKHOD’KO, A.; DECHERT, S.; MEYER, F.
MD
OHdicoppercomplex
OH
OH
1/2
dicoppercomplex
O
O
1/2O2
Chem. Commun. 1005 10072008 -, , 8 ,
43
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Reaction of Diazoalkanes with Bis(phosphino)borate Copper(I) ComplexCu
MANKAD, N.P.; PETERS, J. C.
MD
PPh2B
PCu NH2Mes
t-Bu2
t-Bu2
N2CR2
- NH2Mes
[Ph2BPt-Bu 2] Cu N N CR2
or
CR2Cu[Ph2BPt-Bu 2]
or
Cu NN
CR2
CR2
[Ph2BPt-Bu 2]
B
Chem. Commun. 1061 10632008 -, , 9 ,
Cu-Catalyzed Silylation of Cyclopropenes with (Trifluoromethyl)trimethylsilaneCu
FORDYCE, E. A. F.; WANG, Y.; LUEBBERS, T.; LAM, H. W.
MD
R2R1
R3
+ TMSCF3
Cu(acac)2 (5 mol%)dppe (5 mol%)
THF, r.t.
R2R1
R3TMS
10 examples
66-99% yield
Chem. Commun. 1124 11262008 -, , 9 ,
Preparation of Neutral Organocopper(III) ComplexesCu
BARTHOLOMEW, E. R.; BERTZ, S. H.; COPE, S.; DORTON, D. C.; MURPHY, M.; OGLE, G. A.
MD
(CH3)2CuILi.LiI1) L
2) Et-ICuIII
CH3
CH3
LCH3CH2
THF-d8, -100°C
10 complexes
Chem. Commun. 1176 11772008 -, , 10 ,
Isomerization of Alkyl Grignard Reagents by Fe-Cu Cooperative CatalysisCu
SHIRAKAWA, E.; IKEDA, D.; YAMAGUSHI, S.; HAYASHI, T.
MD
R
MgX
FeCl3 (2.5 mol%)
CuBr (5 mol%)
PBu3 (10 mol%)
THF, -25°C
RMgX
ER
E'
E = ClSiH2Ph, PhCHO, CO2R = Et, Bu, PhX = Br, Cl isomerization ration > 99%
76-82% yield
Fe
Chem. Commun. 1214 12162008 -, , 10 ,
44
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Cu-Catalyzed Carbomagnesiation with Grignard ReagentsCu
TODO, H.; TERAO, J.; WATANABE, H.; KUNIYASU, H.; KAMBE, N.
MD
R'
R'
R'
RMgXLi2CuCl4 (1 mol%)
THF, 25°C
R'
R'
MgXR
RC
MgX
R'8 examples
Mg
Chem. Commun. 1332 13342008 -, , 11 ,
Cu-Mediated Tandem CO Insertion and Annulation of 1,4-Dilithio-1,3-dienesCu
LUO, Q.; WANG, C.; ZHANG, W.-X.; XI, Z.
MD
Li
LiR2
R3
R1
R4
1) 2 CuCl2) CO (1 atm)
2 tBuOOtBu
O
R1
R2
R3
R4
and/or
O O
R1 R1
R2 R2
R4
R3
R4
R3
8 examples
Li
Chem. Commun. 1593 15952008 -, , 13 ,
Cu-Catalyzed Conjugate Addition of Arylboronic Acids to AlkynoatesCu
YAMAMOTO, Y.; KIRAI, N.; HARADA, Y.
MD
+B(OH)2
R1
R2 CO2R3
CuOAc (1-10 mol%)
MeOH, r.t.
R2 CO2R3
R1
20 examples
60-97% yield
R1 = Me, Cl, Br, I, OMe, CHO, Ac, CO2Et, NO2
R2 = Alkyl, Aryl
Chem. Commun. 2010 20122008 -, , 17 ,
Efficient Addition of Alcohols, Amines and Phenol to Unactivated Alkenes Cu
ZHANG, X.; CORMA, A.
BS
AlkenesCatalystAu(III) + CuCl2
Ethers
Secondary Amines
Ethers
Alcohols
Phenol
Primary amines
AuPd
Dalton Trans 397 4032008 -, , 3 ,
45
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Ternary Metal(II) Complexes of Edda and an Intercalating ligandCu
HEE NG C.; KONG, K. C.; VON, S. T.; BALRAJ, P.; JENSEN, P.; THIRTHAGIRI,E.; HAMADA, H.; CHIKIRA, M.
BS
N
N
M
O
NH
NH
O
O
O
M = Cu, Co, Zn,
CoZnNi
Dalton Trans 447 4542008 -, , 4 ,
Tetranuclear Cu(II) PhosphonatesCu
DNA cleavage.
CHANDRASEKHAR, V.; AZHAKAR,R.; SENAPATI, T.; THILAGAR, P.; GHOSH, S.; VERMA, S.; BOOMISHANKAR,R.;STEINER, A.; KÖGERLER, P.
BSDalton Trans 1150 11602008 -, , 8 ,
Highly Efficient Copper-Mediated Atom-Transfer Radical Addition (ATRA) Cu
Addition of polybrominated compounds to alkenes in the presence of AIBN.
ECKENHOFF, W. T.; GARRITY, S. T.; PINTAUER, T.
BS
CuI(TPMA)Br [TPMA = tris(2-pyridylmethyl)amine]
Eur. J. Inorg. Chem. 563 5712008 -, , 4 ,
Trinuclear Copper-PHI Complex Derived from L-Histi dineCu
Cu3(PHI)(N3)x exhobits biomimetic monooxygenase activity towards phenolic substrates.
GULLOTTI, M.; SANTAGOSTINI, L.; PAGLIARIN, R.; PALAVICINI, S.; CASELLA, L.; MONZANI, E.; ZOPPELLARO, G.
BSEur. J. Inorg. Chem. 2081 20892008 -, , 12 ,
46
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
New Copper(II) Tetraazamacrocycle Complexes for Oxidation of PhenolCu
BANSAL, V. P.; KUMAR, R.; PRASAD, R.; PRASAD, S.; NIRAJ.
PLA
NH HN
NH HN
L =
OH H2O2
LCuCl2
OHHO
ortho : para up to 93:7
J. Mol. Catal. A 69 762008 284 -, , 1-2,
Pd-free Sonogashira Coupling of Alkynes with Aryl Halides and Arylboronic AcidsCu
MAO, J.; GUO, J.; JI, S.-J.
PLA
R
R = Aryl, alkyl
+ ArXX = B(OH)2, 14 - 26 %, 6 examples
CuBr, rac-BINOL
Cs2CO3, DMFR Ar
X = I, Br, 23 - 87 %, 10 examplesB
J. Mol. Catal. A 85 882008 284 -, , 1-2,
Zeolite Encapsulated Copper Complexes as Oxidation Catalysts Cu
Encapsulation provides better catalytic activity and lifetime.
SALAVATI-NIASARI, M.
PLA
X
N N
X
R R
Cu2+O-
O-
O-
X = NH, O, S
Na+Na+
Cu([R]2-N2X2)]2+-NaY =
Cu([R]2-N2X2)]2+-NaY
TBHPCOCH3
selectivity up tp 97 %
J. Mol. Catal. A 97 1072008 284 -, , 1-2,
Cu-exchanged Heteropoly Acid as Catalyst for Alkene Cyclopropanation Cu
Reusable catalyst
YADAV, J.S.; SUBBA REDDY, B. V.; PURNIMA, K. V.; NAGAIAH, K.; LINGAIAH, N.
PLA
R1
+ N2CHCO2EtCu-TPA (10 %)
CH2Cl2, R.T.R3
R2
R1
R3
R2
CO2Et
12 examples 80-95 %, trans:cis up to 2.4:1
Cu-TPA:Cu1.5PW12O40 Cu-exchanged
phosphotungstenic acid
W
J. Mol. Catal. A 36 402008 285 -, , 1-2,
47
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Zeolite Encapsulated Copper Complexes as Catalysts for Cyclohexane Oxidation Cu
Encapsulation of Cu-complexes gives better catalytic activity and affords reusable catalysts.
SALAVATI-NIASARI, M.; SOBHANI, A.
PLA
H2O2
[ML]-NaY
M = Cu, Mn, Co, Ni
+
O OH
O-
O-
O-
Na+Na+
[ML]-NaY =
O
NHN NH
N
OM(II)
O O
up to 82.5:17.5 selectivity
MnCoNi
J. Mol. Catal. A 58 672008 285 -, , 1-2,
Cu-Based Catalyst System for the Reactions of Alcohols with Aryl HalidesCu
ALTMAN, R. A.; SHAFIR, A.; CHOI, A.; LICHTOR, P. A.; BUCHWALD, S. L.
BS
X
R1
+ HOR2
OR2
R1
L =N
N
CuI ( 0.05 eq.), L (0.1 eq.)
Cs2CO3, Toluene, 80-130°C, 12-30 h
X = I, Br. R1 = Cl, Br, OMe, CF3 .R2 = Alkyl, Benzyl, Allyl, Propargyl.72-99 %
J. Org. Chem. 284 2862008 73 -, , 1 ,
Conjugation of Nucleosides and OligonucleotidesCu
JAWALEKAR, A. M.; MEEUWENOORD, N.; CREMERS, J. G. O.; OVERKLEEFT H. S.; VAN DER MAREL, G. A.; RUTJES,F. P. J. T.; VAN DELFT, F. L.
BS
OH
A
HO O
O
HO
RN3 (1 eq.), Cu-wire
CH3CN, H2O OH
A
HO O
O
HO
N
N
N
R
yield > 92%
J. Org. Chem. 287 2902008 73 -, , 1 ,
Enantioselective SN2' Allylic Alkylation Catalyzed by Copper-Carbene ComplexesCu
SEO, H.; HIRSCH-WEIL, D.M.; ABBOUD, K. A.; HONG, S.
BS
OPiv
C (0.03 eq.), n-HexMgBr (1.5 eq.)
Et2O, 0°C, 1 h, 91%
n-Hex
+
n-Hex
(SN2)(SN2')
SN2'/SN2 = 85/15
C =N N
Cy CyCuCl
J. Org. Chem. 1983 19862008 73 -, , 5 ,
48
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Validation of the Copper(I)-Catalyzed Azide-Alkyne Coupling in Ionic LiquidsCu
MARRA, A.; VECCHI, A.; CHIAPPE, C.; MELAI, B.; DONDONI, A.
BS
Sugar + N3
Sugarionic liquid, 80°C, 16 h
Sugar N
Sugar
up to 95% yieldCuI (0.5 eq.), i-Pr2EtN (5 eq.)
J. Org. Chem. 2458 24612008 73 -, , 6 ,
Ligandless Microwave-Assisted Pd/Cu-Cat. Arylation of OxazolesCu
BESSELIÈVRE, F.; MAHUTEAU-BETZER, F.; GRIERSON, D. S.; PIGUEL, S.
BS
N
OAr1
Ar2Br (1.2 eq.), Pd(OAc)2 (0.05 eq.), CuI (1 eq.)
K2CO3 (2 eq.), DMF, µW, 150°C 4-15 min.
N
OAr1 Ar2
63-81%
Pd
J. Org. Chem. 3278 32802008 73 -, , 7 ,
Intramolecular C-Arylation of Benzylic CarbonCu
SALCEDO, A.; NEUVILLE, L.; ZHU, J.
BS
NH
N
O
O
I
R1
R2I 1) Cu(I) cat.
2) Pd(0) cat. N
O
N
R2O
R1
Ugi 4CR Adduct up to 60% yield
Pd
J. Org. Chem. 3600 36032008 73 -, , 9 ,
Multicomponent One-Pot Reaction of Azide and Alkyne Mediated by CuI/NBSCu
LI, L.; ZHANG, G.; ZHU, A.; ZHANG, L.
BS
HS P
SPh
O
OO
NH
O
OO
HON3
+CuI (1 eq.), NBS (1 eq.) HS P
SPh
O
OO
NH
O
O
N
N
N
IO
OO
HO
90 %THF, RT, 3 h
J. Org. Chem. 3630 36332008 73 -, , 9 ,
49
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Synthesis of Sugar Triazoles with 1,3-CycloadditionCu
The synthesized sugar triazoles were evaluated for their antitubercular activity.
SINGH, B. K.; YADAV, A. K.; KUMAR, B.; GAIKWAD, A.; SINHA, S. K.; CHATURVEDI,V.; TRIPATHI, R. P.
LS
OO
OMe
Me
N3
OBzlO
N3
OO
Me Me
OMe
ON3
OHOH
OMe
oror
ON
R2R3
R1
NN
RR H
CuSO4 (2 mol %)/sodium ascorbate (5 mol %)/ t-BuOH/H2O (1:1), 30°C, 2.5 to 18 h
(1 eq).
R = Ph, CH2-OH, Bn, alkyl15 Examples
Yield = 60 - 94%
Organometallics 1153 11622008 343 -, , ,
Copper-Catalyzed Binaphtol SynthesisCu
YAN, P.; SUGIYAMA, Y.; TAKAHASHI, Y.; KINEMUCHI, H.; TEMMA, T.; HABAUE, S.
LE
OHR1
R2 R3
CO2PhHO
+
CuCl-(S)Phbox 0.2 eq.Yb(OTf)3 0.1 eq.
O2, THF, rt
OHR1
R2 R3
CO2PhHO
74-99%9-86% ee
Tetrahedron 4325 43312008 64 -, , 19 ,
Copper-Catalyzed Suzuki CouplingCu
The use of iodine as an additive allow the coupling of aryl chlorides
MAO, J.; GUO, J.; FANG, F.; JI, S.-J.
LE
Ar1I Ar2B(OH)2+Cu powder
PEG-400K2CO3
Ar1 Ar2 77-99%
B
Tetrahedron 3905 39112008 64 -, , 18 ,
Copper-Catalyzed Coupling of Aryl Halides with NH-HeterocyclesCu
The coupling of other NH-heterocycles is also described
XI, Z.; LIU, F.; ZHOU, Y.; CHEN, W.
LE
ArX
HetArXor
CuI 0.1 eq, L 0.1 eq.
K2CO3, DMF, 110°CNHN+
NNAr
NNArHet
or
77-98%
65-99%
N
O O
N
L =
Tetrahedron 4254 42592008 64 -, , 19 ,
50
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
N-Arylation of Pyrazole Catalyzed by a Trinuclear Copper ComplexCu
Other azoles, amides and phenols are also coupled
TUBARO, C.; BIFFIS, A.; SCATTOLIN, E.; BASATO, M.
LE
R X NNH
+[Cu] 3mol%
Cs2CO3, DMSO100°C, 24h
NNR
16-93%
Tetrahedron 4187 41952008 64 -, , 19 ,
Asymmetric 1,4-Conjugate Additions of Diethylzinc to ChalconesCu
BIRADAR, D. B.; GAU, H.-M.
TJ
O
R1 R2
O
R1 R2 PPh2
N OH
BnPh
Ph5 mol% Ligand
5 mol% Cu(acac)2
Hex/Et2O-40 °C, 16 h 14 examples
Yield >89%ee 81-97%
Ligand =
+ Et2Zn
Tetrahedron Asymm. 733 7382008 19 -, , 6 ,
Amidation of Allylic and Benzylic AcetatesCu
POWELL, D. A.; PELLETIER, G.
TJ
OAcR1
R2
NH
R3 SR4
O ONR3
SR4
O OR2
R1+
5 mol% Cu(OTf)210 mol% t-BuOOAc
ClCH2CH2Cl25-60 °C
14 examples40-93%
Tetrahedron Lett. 2495 24982008 49 -, , 16 ,
A Tandem Ferrier and Click ReactionCu
YADAV, J. S.; REDDY, B. V. S.; CHARY, D. N.; REDDY, CH. S.
TJ
O
ORRO
ROO
RO
RON
NNRO
RO
RON
NNR
5 mol% Cu(OTf)210 mol% Cu powder
TMSN3, MeCN, rt
+αααα ββββ
R α/β = 3:2 to 9:165-85% Yield
Tetrahedron Lett. 2649 26522008 49 -, , 16 ,
51
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Synthesis of Polyfonctionalized BenzofuransCu
SAKAI, N.; UCHIDA, N.; KONAKAHARA, T.
TJ
R2CHO
OH
NH
R R
Me3Si R1
+
O R1
NR
R5% Cu(OTf)2
5% CuCl
DMAPCH3CN, reflux, 6 h 11 examples
22-91%
R = allyl, -(CH2)5
R1 = H, Ph, C6H13
R2 = H, Me, NO2, Br
Tetrahedron Lett. 3437 34402008 49 -, , 21 ,
3D Coordination Network PolymerAg
RICHARDS, P. I.; BICKLEY, J. F.; BOOMISHANKAR, R.; STEINER, A.
BJL
PN
PNP
N NR2
R2N
R2N NR2
NR2
R2N
R:Ag(I)
3D coordination network
Chem. Commun. 1656 16582008 -, , 14 ,
Selective Ag+/Cu2+ Separation by AdsorptionAg
LAM, K. F.; CHEN, X.; FONG, C. M.; YEUNG, K. L.
BJL
MCM-41 adsorbents functionnalized by amine groups were prepared and used for silver adsorption from solution containing copper.
Cu
Chem. Commun. 2034 20362008 -, , 17 ,
Synthesis of 1,2-Dihydroisoquinoline DerivativesAg
DING, Q.; YU, X;; WU, J.
TJ
CHO1. 2-5 mol% AgOTf
10 mol% proline 4A MS, EtOH, rt
2. NaBH4
15 examplestrace-96%
R1
+ R2-NH2N
R1
R2
R1 = Ph, p-MeOPh, cyclopropylR2 = Ar, n-Hexyl
Tetrahedron Lett. 2752 27552008 49 -, , 17 ,
52
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Ketene Aminals and Tetraaminoallenes: a New Class of LigandsAu
FÜRSTNER, A.; ALCARAZO, M.; GODDARD, R.; LEHNMANN, C. W.
CY
N N
N N
AuPPh3
+SbF6–
AuCl(PPh3), NaSbF6, THF
NMe2
NMe2Me2N
Me2N
Me2N NMe2
Me2N NMe2
+
AuPPh3
SbF6–
AuCl(PPh3), NaSbF6, THF
Angew. Chem. Int. Ed. 3210 32142008 47 -, , 17 ,
Au-Catalyzed Synthesis of Pyrrolo[1,2-a]quinolines in waterAu
LIU, X.-Y.; CHE, C.-M.
CY
NH
OPh
N
OPh
+
(4 equiv)
Au[P(tBu)2(o-biphenyl)]Cl (5 mol%),AgSbF6 (5 mol%), H2O, 75 ºC, 30h
93%
19 examples
Angew. Chem. Int. Ed. 3805 38102008 47 -, , 20 ,
Aerobic Oxidation of AlcoholsAu
The Au-Pt clusters present higher activity and selectivity than the single metal clusters
MIYAMURA, H.; MATSUBARA, R.; SHU KOBAYASHI, S.
BJL
OH
R2R1
O
R2R1
Au/Pt (1 mol%)
rt, O2, BTF/H2O, rt
Au/Pt: gold/platinum alloyed bimetallic clusters supported on a cross-linked polystyrene derivative.67-99%
Pt
Chem. Commun. 2031 20332008 -, , 17 ,
Stable Gold Nanoparticle–DNA ConjugatesAu
SHARMA, J.; CHHABRA, R.; YAN, H.; LIU, Y.
BJL
HN C
S
SRNH2R +
SCS pH 9.0
HN C
S
SR
Colloidal solution of Au nanoparticles
Chem. Commun. 2140 21422008 -, , 18 ,
53
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Elucidating Phenol Mechanism by Labeling ExperimentsAu
HASHMI, A. S. K.; RUDOLPH, M.; SIEHL, H.-U.; TANAKA, M.; BATS, J. W.; FREY, W.
MF
O X
R2
R1
DO
XD
R1
R2
X
R1
R2
OH
AuIII Cat.
Chem. Eur. J. 3703 37082008 14 -, , 12 ,
1,2-Alkyl Migration Catalyzed by Au or Pt CatalystsAu
CRONE, B.; KIRSCH, S. F.
MF
RM
R
OX
M
R
O
R- X+
Au / Pt
Pt
Chem. Eur. J. 3514 35222008 14 -, , 12 ,
Dinuclear Au(I) Complexes Linked by Diethynylpyridine GroupsAu
LI, P.; AHRENS, B.; BOND, A. D.; DAVIES, J. E.; KOENTJORO, O. F.; RAITHBY, P. R.; TEAT, S. J.
BS
R3PAu X
2
R = Ph, Cy.X = 2,5- or 2,6 or 2,5'-pyridine, 2,6'-bipyridine
Dalton Trans 1635 16462008 -, , 12 ,
Catalytic Properties of Au(I) Complexes with 4-Substituted PyridinesAu
First activation of bromoarenes with Au(I) in cross-coupling reaction with boronic acids
LIN, J. C. Y.; TANG, S. S.; SEKHAR VASAM, C.; YOU, W. C.; HO, T. W.; HUANG, C. H.; SUN, B. J.; HUANG, C. Y.; LEE, C.S.; HWANG, W. S.; CHANG, A. H. H.; LIN, I. J. B.
MVI
Br
CH3
B(OH)2 N NMe2Au
H3C2
[AuCl2)]
DMF, K2CO3, RT or 130°C
air or N2
Inorg. Chem. 2543 25512008 47 -, , 7 ,
54
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Annulation of Enynes and AlkynesAu
GORIN, D. J.; WATSON, I. D. G.; TOSTE, F. D.
CJM
Ar
R1
+
OPiv
Ar
R1R1
RAgOTf 5%(ArO)3PAuCl 5%
CH2Cl2, rt
AgSbF6 5%(ArO)3PAuCl 5%
CH2Cl2, rt
J. Am. Chem. Soc. 3736 37372008 130 -, , 12 ,
Cycloisomerization of 1,5-AllenynesAu
CHEONG, P. H.-Y.; MORGANELLI, P.; LUZUNG, M. R.; HOUK, K. N.; TOSTE, F. D.
CJM
•
R3
R1
R2 Ph3PAu
AuPPh3DFT studies
R3
R1
R2
J. Am. Chem. Soc. 4517 45262008 130 -, , 13 ,
Propargylic Pivalates RearrangementsAu
LI, G.; ZHANG, G.; ZHANG, L.
CJM
OPiv
R2iPrAuNTf2 5%
DCE, 80 °CR
OPivR2
R1
J. Am. Chem. Soc. 3740 37412008 130 -, , 12 ,
Double Intramolecular Hydroalkoxylations.Au
Other examples with alkynyl di-phenols.
ZHANG, Y.; XUE, J.; XIN, Z.; XIE, Z.; LI, Y.
MJ
OH
( )m
( )n
OH
OO OO
O
O
( )n
( )n
"Au" (cat.)
CH2Cl2, rt
m = 1, n = 0: 75%m = 1, n = 1: 52% 34%m = 1, n = 1: 84%
Ph3PAuCl (0.02 equiv.)AgOTf (0.02 equiv.)
25-30 minPh3PAuCl (0.1 equiv.)
AgOTf (0.1 equiv.)4 d
m = 1, n = 1: 52%m = 1, n = 1: 72%
Synlett 940 9442008 -, , 6 ,
55
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Cyclization.Au
11 examples. Lower yields using In and Zn catalysts.
YEOM, H.-S.; KIM, S.; SHIN, S.
MJ
NO
Ph
NOH
Ph
catalyst (0.05 eq.)
CH2Cl2, rt, 30 min
Au(IMes)OTf: 96%AgOTf: 85%
Ag
Synlett 924 9282008 -, , 6 ,
Diastereoselective Addition of Silyl Substituted Crotylzinc to Carbonyl CompoundsZn
HELM, M. D. H.; MAYER, P.; KNOCHEL, P.
MVI
SiR3
Me
ZnCl.LiCl
O
RSRLSiR3
RL
OHRS
THF, -78°C
High yieldsHigh diastereoselectivities
Si
Chem. Commun. 1916 19172008 -, , 16 ,
Catalyst Self-Adaptation in Conjugate Addition to Nitroalkenes and NitroacrylatesZn
Tropos ligands more efficient than the atropos analogues
WAKABAYASHI, K.; AIKAWA, K.; KAWAUCHI, S.; MIKAMI, K.
MVI
O
OP
Ph
PhPh
NO2
Et
Et2ZnNO2RMe3Al
EtO2C
NO2
Me+
[2% Cu(OTf)2 + 4% L]R = CO2Et R = Ph
LAl
J. Am. Chem. Soc. 5012 50132008 130 -, , 15 ,
Enantioselective Addition of Arylzinc Reagents under Microwave ConditionsZn
Acceleration of both formation and addition of arylzinc species under these conditions
BRAGA, A. L.; PAIXAO, M. W.; WESTERMANN, B.; SCHNEIDER, P. H.; WESSJOHANN, L. A.
LE
Ar1B(OH)2 Et2Zn+
L (10 mol%)
Ar2CHO
Toluene, MW (300W) Ar1 Ar2
OH
88-98 %
70-98 % ee
L =
N
Tr
OH
PhPhB
J. Org. Chem. 2879 28822008 73 -, , 7 ,
56
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Synthesis of TrimethylsilylalkynesZn
Allows the silylation of functionnalized alkynes
RAHAIM, R. J.; SHAW, J. T.
LE
R H R SiMe3TMSOTf 1.5eq., NEt3 1.5 eq.
Zn(OTf)2 cat.
CH2Cl2, rt81-100%
J. Org. Chem. 2912 29152008 73 -, , 7 ,
Preparation of N-Sulfonyl and N-SulfinyliminesZn
FAN, R.; PU, D.; WEN, F.; YE, Y.; WANG, X.
LE
R1CHO R2SH2N
O X
X = O or :
+PhCH2Br, Zn
THF, rt
R2SN
O X
R1
55-98 %
J. Org. Chem. 3623 36252008 73 -, , 9 ,
Synthesis of Furan Derivatives by Addition of zinc Reagents to 2-Alkynyl AldehydesZn
CHAI, Z.; XIE, Z.-F.; LIU, X.-Y.; ZHAO, G.; WANG, J.-D.
LE
CHO
R1
RZnR', L*rt then reflux
O
R1
R
or O
R1
R
For aromatic cycles For cycloalkenes
59-83 %36-97 %ee
70-75%
NHO
O
O
O
O
Ph
Ph
O Ph
O Ph2
L =
J. Org. Chem. 2947 29502008 73 -, , 7 ,
Mechanism of the Aqueous Barbier Allylation ReactionZn
DAM, J. H.; FRISTRUP, P.; MADSEN, R.
LE
Ar
O
H/DBr+ Met
H2O Ar
OHD/H
Met = Zn, Sn, Sb, Bi, Mg
InSnSbBiMg
J. Org. Chem. 3228 32352008 73 -, , 8 ,
57
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
From Bromohydrins to Ketones Through Zinc-Mediated 1,2-MigrationZn
LI, L.; CAI, P.; GUO, Q.; XUE, S.
LE
OHPhAc
( )n
O
Ph
( )n
Et2Zn 0.6 eq.
CH2Cl2, rt
85-98 %
J. Org. Chem. 3516 35222008 73 -, , 9 ,
Carbometallation of Unactivated Alkenes by Zinc Enolate DerivativesZn
Prospective article (89 references).
PEREZ-LUNA, A.; BOTUHA, C.; CHEMLA, F.
CB
[Zn]
EWG
[Zn]
EWG
Inter or Intra Carbometallation reaction
Stabilized zinc enolate Non stabilizedalkylzinc reagent
New J. Chem. 594 6062008 32 -, , 4 ,
Regioselective Transfer of Prenyl Anion.Zn
Application to the synthesis of (+/-)-Shikonin.
XU, D.-F.; ZHAO, L.-M.; MAO, Z.-Q.; LI, S.-S.
CB
O O
O OCHO
OH O
OH O OH
R
OH
R
R
OH
94% 85%
HMPAor NMP
130°C / 24h
Br
Zn dust
LiClO4
THF
BrZn
(+/-)-Shikonine 80%
CH3CN-H2O
ElectrolyzedPt/3V
Org. Prep. Proc. Int. 93 962008 40 -, , 1 ,
Three-Component Approach to the Synthesis of αααα,αααα-Disubstituted AminesZn
Reactions are conducte.d under Barbier-like conditions using simple organic halides and zinc dust
SENGMANY, S.; LE GALL, E.; TROUPEL, M.
OS
Br
NH2
H
ON
79%
Zn
MeCN, 1 h.+ +
Synlett 1031 10352008 -, , 7 ,
58
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Synthesis and Functionalization of PolyynesZn
Practical synthetic procedures via alkylidene carbenoids.
LUU, T.; MORISAKI, Y.; TYKWINSKI, R.R.
GJ
I OCH3
H
BrBr
Ph
ZnClPhb) ZnCl2
(Ph3P)4Pd
OCH3Ph
a) BuLi (2 equiv)toluene
80%
LiPd
Synthesis 1158 11622008 -, , 7 ,
Enantioselective Addition of Organozinc Reagents to Ketones.Zn
Use of nanosize isoborneol ligands.
FORRAT, V.J.; RAMON, D.J.; YUS, M.
CB
Ar
O
RR'2Zn
Ar
HO
up to 99% ee
5 mol% L* =
+
R'
PhCH3 25°C / 2-7 dR
Ti(O-iPr)4 (1.1 equiv)
HNNHSO2
SO2OH
S-Frechet-dendron
R' = Me, Et, PhR = Me, Et
Ti
Tetrahedron Asymm. 537 5412008 19 -, , 5 ,
Enantioselective Diethylzinc Addition to Aldehydes.Zn
Use of β-hydrosalicylhydrazones ligands.PARROT II, R.W.; DORE, D.D.; CHANDRASHEKAR, S.P.; BENTLEY, J.T.; MORGAN, B.S.; HITCHCOCK, S.R.
CB
Toluene / 25°C / 18h
R
O
H
Et2Zn
R
OH
84-92% ee10 mol% L* =
+
EtHO
NN
OHPh
Me
R1
R2
R3
R4R
R = Ar, CH=CHPh
(3 equiv)
Tetrahedron Asymm. 607 6112008 19 -, , 5 ,
Microwave-assisted Enantioselective Diethylzinc Addition to Aromatic Aldehydes.Zn
Catalysis in the presence of chiral aminonaphtols.
SZATMARI, I.; SILLANPÄÄ, R.; FÜLÖP, F.
CB
(2.5 equiv)
X
H
O
X
Et
X
Et
OH OH
10 mol% L* =ee up to 92%
+Et2Zn
OH
Ph NR
α-Naphtyl
OH
Ph NR
β-Naphtyl
or
Toluene
Tetrahedron Asymm. 612 6172008 19 -, , 5 ,
59
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Hydroxyamide-catalyzed Enantioselective Diethylzinc Addition to Benzaldehyde.Zn
DE LA CASAS ENGEL, T.; MAROTO, B.L.; MARTINEZ, A.G.; DE LA MOYA CERERO, S.
CB
(2 equiv)
H
O
Et
OH
5 mol% L* =48-91% ee
Et2ZnHexane / rt / 5h
+
O N
R
An n = 1 or 2
Tetrahedron Asymm. 646 6502008 19 -, , 6 ,
Zn-Mediated Rh-Catalyzed αααα-Trifluoromethylation of KetonesZn
Mechanism of α-trifluoromethylation is proposed.SATO, K.; YUKI, T.; TARUI, A.; OMOTE, M.; KUMADAKI, I.; ANDO, A.
CC
Me3SiO
R R"
R'
RCF3
R' R"
Oi) ZnEt2 (1 eq), 0°C
ii) RhCl(PPh3)3 (4 mol%) CF3I, DME, rt
Yields = 23 - 84%
Rh
Tetrahedron Lett. 3558 35612008 49 -, , 22 ,
Asymmetric Simmons-Smith Reaction of Allylic Alcohols.Al
Authors propose that the bifunctional character of the catalytic system is responsible for good catalytic performances.
SHITAMA, H.; KATSUKI, T.
GR
R'
R OHAlR2X/L*
ZnEt2 (2eq)CH2I2 (2eq)
R'
R OH**
NH N
OH HO
Ph Ph
L*:
8 examplesquantitative yields
ee up to 95 %
Zn
Angew. Chem. Int. Ed. 2450 24532008 47 -, , 13 ,
Synthesis and Characterization of Aluminium and Zinc ComplexesAl
The synthesis of complexes is supported by pyridine-based N,N,N-chelate ligands. The catalysis of these complexes inεCHAI, Z.-Y.; ZHANG, C.; WANG, Z.-X.
LS
N N
NPh N
Me3Si
Al
R Cl
R = Me, Et N PPh2Ph2P
Me3SiN
NSiMe3Al
EtEt
4 steps, yield = 25%
3 steps, yield = 30%
Organometallics 1626 16332008 27 -, , 7 ,
60
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Reactivity of Stable Silylenes toward Terminal AlkynesSi
The reaction leading to 1 is autocatalyzed by small amounts of 1YAO, S.; VAN WÜLLEN, C.; SUN, X.-Y.; DRIESS, M.
EJ
SiN
N
R
R
H
R'Si
N
N
R
R
SiN
N
R
R
H
R'
R' = H, PhCH CR'
hexane, rt
CH CR'
hexane
R = 2,6-iPr2C6H3
- 78°C1 2
12 82-93%
82-85%
Angew. Chem. Int. Ed. 3250 32532008 47 -, , 17 ,
Highly Substituted beta-Hydroxy-gamma-Lactams From beta-Silyloxy HomoenolatesSi
LETTAN, II, R. B.; WOODWARD, C. C.; SCHEIDT, K. A.
BN
NMe
Me
O
Me
Li
PhO TMS
LDA
THFN
Me
Me
O
Me
PhPh OH
HNP(O)Ph2
NMeMe
Me
O
TMS Ph
O Ph H
NP(O)Ph2Li
Angew. Chem. Int. Ed. 2294 22972008 47 -, , 12 ,
Imine CinnamylationSi
HUBER, J. D.; PERL, N. R.; LEIGHTON, J. L.
BN
NH
SiO
ClMe
Ph Ph
NH
SiO
ClMe
PhPh H Ph
NR
Ph
NHR
PhRu-2
R = CH2Ar, anti/syn > 20:1, 96% eeR = Ar, anti/syn = 1:7, 96% ee
Ru
Angew. Chem. Int. Ed. 3037 30392008 47 -, , 16 ,
Catalytic Asymmetric Silaboration of Acyclic Unsaturated Carbonyl CompoundsSi
WALTER, C.; OESTREICH, M.
BN
EtO
Bun
O
EtO
Bun
O
SiMe2Ph
[Rh(cod)2]OTf (5 mol%)(R)-BINAP (10 mol%)
Me2PhSi-Bpin
Et3N, dioxane/H2O (10:1)50 °C
55%, 99% ee
RhB
Angew. Chem. Int. Ed. 3818 38202008 47 -, , 20 ,
61
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Vinyl Silanes From Aldehydes via a Metalation–Peterson SequenceSi
MCNULTY, J.; DAS, P.
BN
TMS Cl
TMS
TMS Li
TMS PhCHO TMSsBuLi
THF, -78 °C
E:Z > 9:1, 80%
Li
Chem. Commun. 1244 12452008 -, , 10 ,
Palladium-Catalysed Silaboration Reaction of Terminal AlkynesSi
Stereoselective access to the E isomer is also possible
OHMURA, T.; OSHIMA, K.; SUGINOME, M.
BN
BO
OMe
Me
MeMe
SiMe
MeCl C6H13
(PrOi)Me2Si
C6H13
B(pin)
(η3-allyl)PdCl(PPh)3
(1 mol%)
toluene, rt, 1h
then iPrOH, pyr Z
PdB
Chem. Commun. 1416 14182008 -, , 12 ,
Stereoelective Allylation of Carbonyl Compounds With Silyl-Substituted CrotylzincSi
Trapping with aldehydes was also studied
HELM, M. D.; MAYER, P.; KNOCHEL, P.
BN
MeTMS
Cl
Cl MeTMS
Me
TMSZnCl,LiCl
Zn, LiCl
THF, 25 °C18h
Zn
Chem. Commun. 1916 19172008 -, , 16 ,
A Novel Silyloxy Allenolate in The Reaction of Lithiated Diazoesters with AcylsilanesSi
GALLIFORD, C. V.; SCHEIDT, K. A.
BN
Ph
O
Li N2
CO2EtTMS
Ph
O
TMS
CO2Et
N2
Li -N2
Ph
O
CO2Et
COEt
OLi
Ph
TMSO H2O
Li
Chem. Commun. 1926 19282008 -, , 16 ,
62
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Claisen rearrangement/intramolecular hydrosilation approach to medium-ring ethers.Si
MAK, S. Y. F.; CURTIS, N. R.; PAYNE, A. N.; CONGREVE, M. S.; WILDSMITH, A. J.; FRANCIS, C. L.; DAVIES, J. E.;PASCU, S. I.; BURTON, J. W.; HOLMES, A. B.
BN
OO
Et
OTPSSiH
MeMe
OHO
Et
OTPS
HO
OBr Cl
[RhCl(Ph3P)3], THF, rflx
then H2O2, KOH
dr up to 12.8:1 (+)-obtusenyne
Rh
Chem. Eur. J. 2867 28852008 14 -, , 9 ,
Silylene and Germylene Intermediates from Silole and Germole DianionsSi
This mechanism was supported by experimental data and theoretical calculations
TOULOKHONOVA, I.S.; TIMOKHIN, V.I.; BUNCK, D.N.; GUZEI, I.; WEST, R.; MÜLLER, T.
EJ
ELi2
PhPh
PhPh
NtButBuNTHF/rt
E:
PhPh
PhPh
NtButBuN
Li Li
NtButBuN
E
PhPh
PhPh
N
N
tBu
tBu
_
E = Si, Ge
55-63%
GeLi
Eur. J. Inorg. Chem. 2344 23492008 -, , 14 ,
Efficient Palladium-Catalysed Silylation Reaction of ArI Si
IIZUKA, M.; YOSHINORI, K.
BN
NC
I
SiMe2H
OTHP
NC
Me2Si
OH
Pd(OAc)2, pyridineLiCl, DMI, rt, 24hthen PTSA, MeOH 59%
Pd
Eur. J. Org. Chem. 1161 11632008 -, , 7 ,
Silylene Equivalents And Alkyne: Expeditive Access to 2,4-Disubstituted SilolesSi
OHMURA, T.; MASUDA, K.; SUGINOME, M.
BN
BO
OMe
Me
MeMe
SiMe
MeEt2N C6H13
SiMe2
C6H13
C6H13Pd(dba)2 (1 mol%)
P(t-Bu)2(2-biphenyl) (1.2 mol%)
toluene, rt74%
PdB
J. Am. Chem. Soc. 1526 15272008 130 -, , 5 ,
63
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
General Rhodium-Catalyzed Asymmetric Alkynylation ReactionSi
The sterically bulky substituents on Si and P are required to avoid alkyne dimerization
NISHIMURA, T.; GUO, X.-X.; UCHIYAMA, N.; KATOH, T.; HAYASHI, T.
BN
O
O PAr2
O
O
PAr2 OMetBu
tBu
Ph Me
O
TIPS
Ph
O Me
TIPS
[Rh(µ-OAc)(C2H4)2]2 (5 mol% Rh)
(R)-DTBM-segphos (5.5 mol%)
Dioxane80 °C, 12h, 99%
(R)-DTBM-segphos
Ar =
Rh
J. Am. Chem. Soc. 1576 15772008 130 -, , 5 ,
Stereospecific Chromium-Promoted Silyl Cyclopropanation of Unsaturated AmidesSi
CONCELLON, J. M.; RODRIGUEZ-SOLLA, U.; MEJICA, C.; BLANCO, E. G.; GARCIA-GRANDA, S.; DIAZ, M. R.
BN
C5H11 CONMe2
TBS
C5H11 CONMe2
CrCl2Br2CHSitBuMe2
THF, rt
Cr
Org. Lett. 349 3522008 10 -, , 2 ,
Theoretical Studies of the Thermal Rearrangement of Silylene Me3SiSiHSi
The energy barrier for the CH insertion by the silylene are predicted to be 12.7 kcal/mol
BOO, B.H.; IM, S.; PARK, S.; LEE, S.
EJ
R
R M
R = tBuRC P
Et2OMP4C4R4
-70°C to rt
M = Ge, 43%
M = Sn, quantitative, but unstable compound
Organometallics 2123 21272008 27 -, , 9 ,
Complexes of Germanium (IV) Fluoride with Phosphane LigandsGe
Complexes have also been made between AsR3 and GeF4 or GeCl4DAVIS, M.F.; LEVASON, W.; REID, G.; WEBSTER, M.
EJ
GeF4(MeCN)2
PR3
CH2Cl2/rttrans-[GeF4(PR3)2]
R2P(CH2)2PR2
CH2Cl2/rtcis-[GeF4(R2P(CH2)2PR2)] 40 to 90%
PAs
Dalton Trans 2261 22692008 -, , 17 ,
64
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Synthesis and Theoretical Studies of a Novel Organophosphorus Cage CompoundGe
DFT calculations support the reaction pathway
FRANCIS, M.D.; HITCHCOCK, P.B.; NIXON, J.F.; NYULASZI, L.
EJ
R
R M
R = tBuRC P
Et2OGeP4C4R4
-70°C to rt
M = Ge, 43%
M = Sn, quantitative, but unstable compound
SnP
Eur. J. Inorg. Chem. 1761 17662008 -, , 11 ,
Synthesis of Aluminogermanate NanotubesGe
Structural analogy with imigolite Al2SiO3(OH)4
LEVARD, C.; ROSE, J.; MASION, A.; DOELSCH, E.; BORSCHNECK, D.; OLIVI, L.; DOMINICI, C.; GRAUBY, O.; WOICIK,J.C.; BOTTERO, J.-Y
EJ
Et4-orthosilicate
Et4-orthogermanate/AlClO4
Ge-imigoliteNaOHrt/12h then 95°C/5d
Al
J. Am. Chem. Soc. 5862 58632008 130 -, , 18 ,
Hydrogermolysis Reactions Involving Germylated NitrilesGe
Compound 2 tBu3GeGePh3 could not be obtained due to the too large steric hindrance
AMADORUGE, M.L.; DIPASQUALE, A.G.; RHEINGOLD, A.L.; WEINERT, C.S.
EJ
R3GeClLiCH2CN
THFR3GeCH2CN
Ph3GeH
CH3CNR3Ge GePh3
R = Ph, iPr, tBu
-78°C to rt 85°C/2d62-70% 87-90%
1 2
1:
2: R = Ph, iPr
Li
J. Organomet. Chem. 1771 17782008 693 -, , 10 ,
Synthesis, Structure and Reactivity of OligogermanesGe
From 1, F3CSO3H, LiAlH 4 and again CH3CN and PhGeH3, oligogermanes are obtained
AMADORUGE, M.L.; GOLEN, J.A.; RHEINGOLD, A.L.; WEINERT, C.S.
EJ
Ph3GeNMe2
CH3CNPh3GeCH2CN
PhGeH3
CH3CN85°C/48h
PhGe(GePh3)3 85%
1
LiAl
Organometallics 1979 19842008 27 -, , 9 ,
65
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Distannylation and Silastannylation of In situ Generated AllenesSn
WESQUET, A. O.; KAZMAIER, U.
LGE
RO
ROSnBu3
Bu3SnSnBu3
Bu3SnH, Pd(0)
Bu3SnH, Mo(0)
Bu3SnH, Pd(0)
Si
Angew. Chem. Int. Ed. 3050 30532008 47 -, , 16 ,
Oxidation of the Stannole DianionSn
HAGA, R.; SAITO, M.; YOSHIOKA, M.
LGE
Sn
Ph
Ph
Ph
Ph
Li Li
O2 (1.3 equiv.) 81 %
Li (quantitatif)
Sn
Ph
Ph
Ph
Ph
Li
Sn
Ph
Ph
Ph
Ph
Sn
Ph
Ph
Ph
Ph
Li
Li
Chem. Eur. J. 4068 40732008 14 -, , 13 ,
Reactivity of the Tin-Carbon Bond of an Almost Planar StanneneSn
Stannene 1, the X-ray crystal structure of which is reported, reacts with crotonaldehydes by a [2+4] cycloaddition.
FATAH, A.; AYOUBI, R.E.; GORNITZKA, H.; RANAIVONJATOVO, H.; ESCUDIÉ, J.
TT
CSn
O CHMe
H H
TipTip R2
iPr
iPr
iPr
Tip2SnF2 Tip2Sn = CR2
CH3CH=CH-CHOCR2 = Tip =
2 steps
1
tBu
tBu
Eur. J. Inorg. Chem. 2007 20132008 -, , 12 ,
Crotylation of Aldehyde by CrotyltinsSn
The reaction between aldehydes and crotyltins is highly dependant on the nature of aldehyde, metal salt and solvent
FARGEAS, V.; ZAMMATTIO, F.; CHRÉTIEN, J.-M.; BERTRAND, M.-J.; PARIS, M.; QUINTARD, J.-P.
LGE
SnBu3+ RCHO
Lewis acid
Solvent
R
OH
Z or E
R
OH
syn or antiLewis Acid : BF3.OEt2, InCl3, InBr3, CeCl3.7H2OSolvent : CH2Cl2, CH3CN
+
Simple Lewis acid assistance on the aldehyde = syn + ZTransmetallation before addition to the aldehyde = anti + E
CeIn
Eur. J. Org. Chem. 1681 16882008 -, , 10 ,
66
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
An Efficient Catalyst for Ring-Opening Polymerization of εεεε-CaprolactoneSn
1 catalyzes efficiently the polymerization of ε-caprolactone with low tin residues in the final products.POELMANS, K.; PINOIE, V.; VERBRUGGEN, I.; BIESEMANS, M.; DESHAYES, G.; DUQUESNE, E.; DELCOURT, C.;DEGÉE, P.; MILTNER, H.E.; DUBOIS, P.; WILLEM, R.
TT
O
OOH
P (CH2)11 SnCl3
O
(CH2)5-O-HCH3-CH2-CH2-Oncatalyst 1
1
Organometallics 1841 18492008 27 -, , 8 ,
Optically Active Organotin Compounds for Chiral PolystannanesSn
The chiral information of the myrtanyl group is transferred onto the polymer backbone.
BECKMANN, J.; DUTHIE, A.; GRASSMANN, M.; SEMISCH, A.
TT
SnR R
R2SnCl2 R2SnH2
i) LiAlH 4
ii) H2O
[(Ph3P)3RhCl] cat.
- H2 n
R = cis-Myr
R = trans-Myr
Organometallics 1495 15002008 27 -, , 7 ,
From Lead Selenide to Heterostructured NanocrystalsPb
PIETRYGA, J.M.; WERDER, D.J.; WILLIAMS, D.J.; CASSON, J.L.; SCHALLER, R.D.; KLIMOV, V.I.; HOLLINGSWORTH,J.A.
EJ
PbOOleic acid
Trioctylphosphine
PhOPh
lead selenide nanocrystals
150°C
205°C
Trioctylphosphine Se
J. Am. Chem. Soc. 4879 48852008 130 -, , 14 ,
Direct Conversion of Acetonides into DiacetatesBi
WU, .Q.-P.; ZHOU, M.-X.; XI, X.-D.; SONG, D.; WANG, Y.; LIU, H.-X.; LI, Y.-Z.; ZHANG, Q.-S.
CC
O
OO
O
O
RO
AcOAcO O
OAc
O
ROOAc
AcOAcO O
OAc
OAc
RO
AcO
AcOO
O
O
RO
Bi(OTf)3.xH2O(5 mol%),
Ac2O (3 eq),CH2Cl2, rt
Bi(OTf)3.xH2O(15 mol%),
Ac2O (3 eq),CH2Cl2, rt
Bi(OTf)3.xH2O(5 mol%),
Ac2O (3 eq),CH2Cl2, rt89% 85% 85%
Tetrahedron Lett. 2714 27182008 49 -, , 17 ,
67
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Hydrosilylation Reactions Catalyzed by Copper, Silver, and Gold ComplexesRv
DIEZ-GONZALEZ, S.; NOLAN, S. P.
BN
Si
Acc. Chem. Res. 349 3582008 41 -, , 2 ,
Catalytic C-C, C-N, and C-O Ullmann-Type Coupling ReactionsRv
MONNIER, F.; TAILLEFER, M.
MF
UllmannBreakthroughR
X NuR
Nu
Enantioselectivity
Orthogonal Selectivity
Cu Cat.Cu
Angew. Chem. Int. Ed. 3096 30992008 47 -, , 17 ,
The Challenges of the Silylmetalation ReactionsRv
NAKAMURA, S.; YONEHARA, M.; UCHIYAMA, M.
BN
Si
Chem. Eur. J. 1068 10782008 14 -, , 4 ,
Tris(trimethylsilyl)silane: A Versatile ReagentRv
CHATGILIALOGLU, C.
BN
Si
Chem. Eur. J. 2310 23202008 14 -, , 8 ,
68
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Metallosupramolecular Chemistry.Rv
PREFACE FROM LEONARD F. LINDOY.
MJ
Special issue14 articles
Coordin. Chem. Rev. 812 10502008 252 -, , 8, 9,
Bis-Phosphorus Stabilised Carbene ComplexesRv
A perspective article
CANTAT, T.; MÉZAILLES, N.; AUFFRANT, A.; LE FLOCH, P.
MVI
PPR RR R
[M]
PPR RR R
X X
[M]
X = O, NR, S
Dalton Trans 1957 19722008 -, , 15 ,
Light-emitting Iridium Complexes with Tridentate Li gandsRv
A perspective article
WILLIAMS, J. A. G.; WILKINSON, A. J.; WHITTLE, V. L.
MVI
N
N N
N
Ir
N N
N
N N
N
Ir
Dalton Trans 2081 20992008 -, , 16 ,
Cobalt-Rhodium Heterobimetallic Nanoparticle-Catalyzed ReactionsRv
A perspective article
PARK, J. H.; CHUNG, Y. K.
MVI
Co2Rh2
Nanoparticles
Pauson-Khand Reaction Pauson-Khand Type Reaction
SilylcarbocyclizationAminocarbonylation
Hydroformylation
Cyclohydrocarbonylation
Dalton Trans 2369 23782008 -, , 18 ,
69
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Suzuki–Miyaura Cross-Coupling ReactionsRv
DOUCET, H.
BJL
A microreview on the development and advances in Pd-catalyzed coupling of aryl, alkenyl or alkyl halides with alkylboronic acids. The remaining challenges in the field are discussed (101 refs).
Pd
Eur. J. Org. Chem. 2013 20302008 -, , 12 ,
Cross-Coupling–Elimination Reactions Mediated or Catalyzed by Zr ComplexesRv
FAÑANÁS, F. J.; RODRÍGUEZ, F.
OC
54 references
Zr
Eur. J. Org. Chem. 1315 13292008 -, , 8 ,
Use of Samarium Diiodide in the Field of Asymmetric Synthesis.Rv
GOPALAIAH, K.; KAGAN, H.B.
CB
Review (65 References)
New J. Chem. 607 6372008 32 -, , 4 ,
Transition Metal-catalyzed Hydrosilylation of Carbonyl Compounds and Imines.Rv
DIEZ-GONZALEZ, S.; NOLAN, S.P.
CB
Review (156 References)
Org. Prep. Proc. Int. 523 5592007 39 -, , 6 ,
70
Bibliographic Notebooks For Organometallic Chemistry 2008, 26, ( 4)
Arylation, Pd-Catalyzed Aromatic C-H Activation.Rv
LI, B.-J.; YANG, S.-D.; SHI, Z.-J.
MJ
Y
Y = C, N, O .....
Pd catalysis
>54 references
Synlett 949 9572008 -, , 7 ,
Recent Advences in Synthesis of Heterocycles and Cycles via Gold Catalysis.Rv
Heteroatom addition and hydroarylation reactions of alkynes, allenes and alkenes is reported.
SHEN, H. C.
AM
Report (84 references)
Au
Tetrahedron 3885 39032008 64 -, , 18 ,
71