no5 hyousi s - 和光純薬工業株式会社 試薬・臨床検査 … 1 固定化触媒...
TRANSCRIPT
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Chemoselective Reduction Catalysts Set
Pd/C
Pd/C
Pd/C
en1Pd/Fib2
Pd/PEI3
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5
Palladium-Activated Carbon Ethylenediamine ComplexPd3.5-6.5% 5% Pd/C(en) 1g
Palladium-Activated Carbon Ethylenediamine ComplexPd8.5-11.5% 10% Pd/C(en) 1g
Palladium-Fibroin Pd/Fib 1g
Palladium-Polyethyleneimine Pd/PEI 1g
Osmium-Activated CarbonOs 3.5-6.5% Os/C 1g
-Pd/Cen
1 Pd/C 2 3 Pd/C
-Pd/Fib
1 2.5% Pd 2 3Pd/Cen
-Pd/PEI
1 2
-Os/C
1 2 3
5% Pd/Cen 10% Pd/Cen
Pd/C(en)
Pd/Fib
Pd/C Reducible Functionalities
R-OTBDMS(TES) Benzyl alcohol
R-CO2Bn
R-OBn ArCOR aromatic-N-Cbz
epoxide olefin
alkyl-N-Cbz Ar-X ArNO2
R-N3acetylene
Pd-PEI
Reducible Functionalities
R-OBn
ArCOR
Ar-X
aromatic-N-Cbz olefin
alkyl-N-Cbz
acetylene ArNO2
Os/C
OBn OBn
5% Pd/C(en)
H2 (1 atm), MeOH, 24 h
yield 91%
O10% Pd/C(en)
H2 (1 atm), MeOH, 3 h
yield 91%
OH
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2
Pd/Fib Pd/PEI Os/C
No. ()
Chemoselective Reduction Catalysts Set 032-21041 1 19,000
1H. Sajiki, K. Hattori, K. HirotaJ. Org. Chem., 63, 7990 (1998).
2H. Sajiki, T. Ikawa, H. Yamada, K. Tsubouchi, K. HirotaTetrahedron Lett., 44, 171 (2003).
3H. Sajiki, S. Mori, T. Ohkubo, T. Ikawa, A. Kume, T. Maegawa, Y. MonguchiChem. Eur. J., 14, 5109 (2008).
Osmium-Activated CarbonOs/C -
-
Os/C
1gMeOH10ml5% Os/C 100mg NH2NH2H2O 2ml60 4 5% Os/C 2
No. ()
151-02881 1g 5,000 Osmium-Activated CarbonOs 3.5-6.5% Os/C
157-02883 5g 16,000
Pd/Fib
H2 (1 atm), MeOH, 20 hyield 98 %Cl
Ph
O
Cl
Ph
O
PhPhH2 (1 atm), 24 h
MeOH + dioxane (1 : 1)
PhPh +Ph
Ph
Pd/PEI+ Ph Ph
97 1 2: :
O2NOs/C, NH2NH2. H2O (excess)
MeOH, 60 oC, 4 h
H2N
yield 94 %
Os/C
Reducible FunctionalitiesR-OBn
alkyl-N-Cbz
Ar-X
aromatic-N-Cbz
Ar-NO2
olefin
acetylene
ArCOR
O2N Os/C, NH2NH2. H2O (excess)
MeOH, 60 oC, 4 h
H2N
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3
Pd/Cen -
Pd/C
Pd/C
Pd/C(en)1)
Pd/C
-Pd3.56.5 Palladium-activated Carbon-Ethylenediamine ComplexPd3.56.5
5Pd/C(en)2)Cbz(benzyloxy-
carbonyl) 2),3)O-TBDMS(t-butyldimethylsilyl) 4) 5) 6)
1)
1 2 2Cbz 2,3 3 6
No. ()
163-21441 1g 4,000
169-21443 5g 13,500 Palladium-Activated Carbon Ethylenediamine ComplexPd3.5~6.5%
161-21442 25g 46,000
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4
-Pd8.511.5 Palladium-activated Carbon-Ethylenediamine ComplexPd8.511.5
5Pd/C(en) Pd
1,2- 7) 8)O-TBDMS 9)
1)
11,2- 7 2 8 3O-TBDMS 9
No. ()
167-23301 1g 5,000 Palladium-Activated Carbon Ethylenediamine ComplexPd8.5~11.5%
163-23303 5g 16,000
1, : , 59, 109 (2001).
2H. Sajiki, K. Hattori, K. Hirota: J. Org. Chem., 63, 7990 (1998).
3K. Hattori, H. Sajiki, K. Hirota: Tetrahedron, 56, 8433 (2000).
4K. Hattori, H. Sajiki, K. Hirota: Tetrahedron Lett., 41, 5711 (2000).
5H. Sajiki, K. Hattori, K. Hirota: Chem. Eur. J., 6, 2200 (2000).
6H. Sajiki, K. Hattori, K. Hirota: J. Chem Soc., Perkin Trans. 1, 4043 (1998).
7H. Sajiki, K. Hattori, K. Hirota: Chem. Commun., 1041 (1999).
8K. Hattori, H. Sajiki, K. Hirota: Tetrahedron, 57, 4817 (2001).
9K. Hattori, H. Sajiki, K. Hirota: Tetrahedron, 57, 2109 (2001).
OOH10% Pd/C(en)
H2 (5 atm), MeOH, 24 hyield 81%
O10% Pd/C(en)
H2 (1 atm), MeOH, 3 h
yield 91%
OH
OTBDMS10% Pd/C(en)
H2 (1 atm), MeOH, 3 h
yield 93%
OTBDMS
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5
Pd/Fib Pd
- Palladium- FibroinPd/Fib
2.5% Pd 1)3)
Pd/C(en)
2) Cbz(benzyloxy-
carbonyl) 2) 1) 1)
3) 4)
1 2 Cbz 3 4
No. ()
167-22181 1g 4,500 Palladium-Fibroin Pd/Fib
163-22183 5g 14,000
1H. Sajiki, T. Ikawa, H. Yamada, K. Tsubouchi, K. Hirota: Tetrahedron Lett., 44, 171 (2003).
2H. Sajiki, T. Ikawa, K. Hirota: Tetrahedron Lett., 44, 8437 (2003).
3T. Ikawa, H. Sajiki, K. Hirota: Tetrahedron, 61, 2217 (2005).
4, , : , 63, 1218 (2005).
yield 97%
CO2Bn CO2Bn
N3 H2N
2.5% Pd/Fib
H2(1atm), MeOH, rt, 17h
2.5% Pd/Fib
H2(1atm), MeOH, rt, 3hyield 100%
yield 100%
O O
CHO
O
CHO
O
2.5% Pd/Fib
H2(1atm), AcOEt, rt, 27h
NHCbz NHCbz2.5% Pd/Fib
H2(1atm), THF, rt, 5hyield 92%
yield 100%Br Br
2.5% Pd/Fib
H2(1atm), MeOH, rt, 24h
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6
Pd/PEI
- Palladium- PolyethyleneiminePd/PEI
Lindlar
1)
-Pd/PEI2)Pd/C(en)3) Pd/Fib4)
1Partial Hydrogenation of di-substituted Alkynes 2Partial Hydrogenation of mono-substituted Alkynes
No. ()
161-22221 1g 8,000 Palladium-Polyethyleneimine Pd/PEI
167-22223 5g 26,000
1P. N. Rylander, Hydrogenation Methods; Academic Press: New York, 1985.
2H. Sajiki, S. Mori, T. Ohkubo, T. Iwata, A. Kume, T. Maegawa, Y. Monguchi : Chem. Eur. J., 14, 5109 (2008).
3H. Sajiki, K. Hattori, K. Hirota : J. Org. Chem., 63, 7990 (1998).
4H. Sajiki, T. Ikawa, K. Hirota : Tetrahedron Lett., 44, 8437 (2003).
NHCH2CH2 NCH2CH2
CH2CH2NH2x y
Polyethyleneimine(PEI)
Pd(OAc)2/ H2
MeOHPEI-Pd
Ph Ph Ph CO2H Ph CO2Et
33
OH
2
OHHO
97 % 96 % 94 %
100 % 100 % 100 %
OH
Ph
OBn NHCbz
OH
CO2H CO2Bn
HO
91% 96 % 93 % 88 %
84 % 84 % 100 %
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Calcium Vanadate ApatiteVAP
Michael
1Michael
aDetermined by GC using an internal standard technique. Values in parentheses are isolated yields. 2 b
Isotopic[D]:[H] ratio (%)c Substrate Product
First run Second run
90 100
89
94 100
86
79 98
88
bSubstrate(5mmol), VAP(0.05g), D2O(5ml), 50C, 2h, Ar. cDetermined by 1H NMR. Values in parentheses are isolated yields.
No. ()
037-20751 1g 6,000 Calcium Vanadate Apatite VAP
033-20753 5g 18,000
1T. Hara, S. Kanai, K. Mori, T. Mizugaki, K. Ebitani, K. Jitsukawa, K. Kaneda: J. Org. Chem., 71, 7455-7462 (2006).
O
CH3
H3C CH3
H H
O
H H
OH
H
H
H
O
CD3
H3C CH3
D D
O
D D
OD
D
D
D
O
CO2Et+
O VAP
H2O, 30 , 10min
O
CO2Et
O
yielda) >99%(96%)
CO2Et
O
+
O VAP
H2O, 30 , 1.5h CO2Et
O O
yielda) >99%
O
O
CH3
O
+OCH3
O VAP
H2O, 50 , 2h O
O
OCH3
O
O
CH3
yielda) 94%
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8
Homodinuclear Ni2-Schiff Base Catalyst 2
2
(R )-Homodinuclear Ni2-Schiff
Base Catalyst1
anti-
(R)-Homodinuclear Ni2-Schiff Base Catalyst1 (S)-Homodinuclear Ni2-Schiff Base Catalyst C34H20N2Ni2O4637.92 C34H20N2Ni2O4637.92
Ni2
No. ()
087-09011 100mg 8,500 (R)-Homodinuclear Ni2-Schiff Base Catalyst
083-09013 500mg 31,000
084-09021 100mg 8,500 (S)-Homodinuclear Ni2-Schiff Base Catalyst
080-09023 500mg 31,000
1,77(2),5-7(2009).
2Z. Chen, H. Morimoto, S. Matsunaga, M. ShibasakiJ. Am. Chem. Soc., 130, 2170 (2008).
NiO
NN
ONi
OO
NiO
NN
ONi
OO
imine nitroacetate cat temp time yield dr %ee
entry R1 R2 (x mol %) () (h) (%) (anti /syn ) (anti )1 Ph- Me 5 0 12 95 91:9 982 4-MeO-C6H4- Me 5 0 12 92 87:13 98
3 4-Me-C6H4- Me 5 0 12 90 89:11 97
4 4-Cl-C6H4- Me 5 0 12 87 86:14 97
5 4-F-C6H4- Me 5 0 12 91 90:10 91
6 3-thienyl- Me 5 0 12 96 91:9 997 Ph- Et 5 0 12 91 94:6 998 Ph- n Pr 5 0 12 92 92:8 >999 Ph- Bn 5 0 12 94 88:12 94
10 PhCH2CH2- Me 10 -40 36 73 >97:3 95
11 n -butyl Me 10 -40 36 67 >97:3 9312 i -butyl Me 10 -40 24 85 >97:3 9113 Ph- Me 1 rt 12 93 88:12 98
NBoc
R1
+ R2CO2tBu
NO2
(R)-Ni2/1(x mol %)
THF,MS 4,temp
BocNH
R1CO2tBu
R2 NO2(1.1-2.0 equiv)
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()
()
2
OsmiumOxide, MicroencapsulatedMC OsO41
N -- N NMO
No. ()
Osmium()Oxide, Microencapsulated MC OsO4 153-02081 1g 15,000
MC OsO4() OsO4 OsO4(50mg) MC OsO4(OsO4 50mg)MC OsO4 3
Blank
3days 2min
MC OsO4OsO4 BlankMC OsO4OsO4
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10
PEM OsmiumOxide, PEM MicroencapsulatedPEM-MC OsO42
K3Fe(CN)6
PEM (Phenoxy-
ethoxymethyl-polystyrene) PEM
(K3Fe(CN)6)
No. ()
Osmium() Oxide, PEM-Microencapsulated PEM-MC OsO4 158-02411 1g 20,000
1S. Kobayashi, M. Endo, S. Nagayama : J. Org. Chem., 63, 60941998.
2S. Kobayashi, T. Ishida, R. Akiyama : Org. Lett., 3, 26492001.
PEM-polystyrene
OOPh
x y
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11
Os IC-I
()
()
()
(Os IC-I)
1NMO
2K3Fe(CN)6
No. ()
153-02581 5g 13,000 Osmium Oxide, Immobilized Catalyst I Os IC-I
151-02582 25g 50,000
NMO (1.5 eq)rt, 12 h
OHOH
Os IC-I (5 mol%)
NMO (1.5 eq)Acetone-H2O-CH3CN (1/1/1)
rt, 12 h
Os IC-I (5 mol%)
Entry
1234
Solv.
H2O/THF (1/1)H2O/CHCl3 (1/1)H2O/AcOEt (1/1)
H2O/toluene/CH3CN (1/1/1)
Yield (%)
85738188
Run
Yield of Product (%)ee (%)
1
8592
2
8592
3
8390
OHOHOs IC-I(5mol%)
(DHQ)2PHAL(5mol%)
K3Fe(CN)6(3 eq)K2CO3(3 eq)
t-BuOH-H2O(1/1), rt, 16 h
OHOH
Run
Yield of Product (%)
1
84
2
83
3
83
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12
FibreCat
120 150
11000 Pd Heck
23000 RuOs
No. ()
324-56621 1g 7,000 FibreCat 1001 (Palladium() Acetate-Triphenylphosphine PE fibres)
Pd 48320-56623 5g 24,000
321-56631 1g 8,000 FibreCat 1007 (Palladium() Acetate-Dicyclohexylphenylphosphine PE fibres)
Pd 48327-56633 5g 29,000
328-56641 1g 7,000 FibreCat 1026 (Acetonitrile Dichloropalladium()-Triphenylphosphine PE fibres)
Pd 48324-56643 5g 24,000
325-56651 1g 7,000 FibreCat 2003 (Bis( -norbornadiene)rhodium()Tetrafluoroborate-Triphenylphosphine PE fibres)
Rh 36321-56653 5g 24,000
322-56661 1g 7,000 FibreCat 2006 (Di--chlorobis(-norbornadiene)dirhodium()-Triphenylphosphine PE fibres)
Rh 36328-56663 5g 24,000
329-56671 1g 7,000 FibreCat 3002 (Sodium Ruthenate()-Triethylamine PE fibres)
Ru 36325-56673 5g 24,000
326-56681 1g 7,000 FibreCat 3003 (Osmium() Oxide-Pyridine PE fibres)
Os 36322-56683 5g 24,000
323-56691 1g 7,000 FibreCat 3004 (Dipotassium Dioxotetrahydroxoosmate()-Triethylamine PE fibres)
Os 36329-56693 5g 24,000
326-56701 1g 7,000 FibreCat 4001 (Dihydrogen Hexachloroplatinate() n-Hydrate-Pyridine PE fibres)
Pt 36322-56703 5g 24,000
323-56711 1g 7,000 FibreCat 4003 (cis-Bis(acetonitrile)dichloroplatinum()-Triphenylphosphine PE fibres)
Pt 36329-56713 5g 24,000
FibreCat Johnson Matthey
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13
Pt IC-I
50
No. ()
167-22701 1g 4,000 Platinum, Immobilized Catalyst I Pt IC-I
163-22703 5g 12,000
1 , , , , 49, 211 (2007).
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14
Precious Powder Metal Catalysts
No. ()
355-13071 5g 6,000 5% Palladium on Activated Carbon, Degussa type E105 O/W 5%Pd(wetted with ca.55% water)
353-13072 25g 18,000
324-81651 5g 3,500 5% Palladium on Activated Carbon, Degussa type E101 NE/W 5%Pd(wetted with ca.55% water)
322-81652 25g 11,000
358-13061 5g 6,000 5% Palladium on Activated Carbon, Degussa type E106 R/W 5%Pd(wetted with ca.55% water)
356-13062 25g 18,000
351-13051 5g 6,000 5% Palladium on Activated Carbon, Degussa type E105 NN/W 5%Pd(wetted with ca.55% water)
C=C 359-13052 25g 18,000
352-13081 5g 7,000 3% Platinum on Activated Carbon, Degussa type F1015 RCA/W 3%Pt(wetted with ca.55% water)
350-13082 25g 23,000
354-13122 5g 6,500 1% Platinum+0.1%Copper on Activated Carbon, Degussa type CF105 R/W 1%Pt+0.1%Cu(wetted with ca.55% water)
358-13125 25g 20,000
OCH2Ph
OCH2Ph
R
OH
OHR
E 105 NN/W 5Pd
E 101 NE/W 5Pd
E 106 R/W 5Pd
E 105 O/W 5Pd
F 1015 RCA/W 3Pt
CF 105 R/W 1Pt+0.1Cu
X=Cl, Br, l, F
OH
O
R
OH
O
R
NO2
R
NH2
R
NO2
X
NH2
X
R R
R1 R2
NR3
R1 R2
NHR3
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15
RuHAP-Fe2O3
[HAPCa10(PO4)6(OH)2] RuCl
RuHAP()
Fe2O3
Oxidation of Various Alcohols Catalyzed by RuHAP- Fe2O3 under 1 and 5 atm of Molecular Oxygena
entry substrate O2 pressure[atm] time[h]
conv.[%]
yield[%]
TOF[h-1]
1 2
1 5
1 0.5
>99>99
9894
196376
3 4
1 5
2 1
>99>99
9999
99198
5 6
1 5
2 1
9595
9195
91160
7 8
1 5
1 0.5
>99>99
9898
196392
9 10
1 5
6 3
>99>99
>9996
3364
11[b] 12[b]
1 5
2.51.25
91>99
8696
3477
13[c] 14[c]
1 5
9 9
>99>99
>98[d]
>99[d]1111
15[c] 16[c]
1 5
1210
8792
8391
79
17 18
1 5
2 1
>9989
>9981
100162
19[b] 20[b]
1 5
1515
8995
8895
66
21[b] 22[b]
1 5
5 2.5
>99>99
9698
1939
aAlcohol (1mmol), RuHAP-Fe2O3 (0.5mol%), toluene (5ml), 90, O2 flow. bRuHAP-Fe2O3 (1mol%). cRuHAP-Fe2O3 (1mol%), ,,,-trifluorotoluene (5ml). d1-Dodecanoic acid was formed.
No. ()Ruthenium()-Hydroxyapatite Encapsulated Superparamagnetic Maghemaite
RuHAP-Fe2O3 187-02261 500mg 16,000
1K.Mori, S.Kanai, T. Hara, T.Mizugaki , K.Ebitani, K.Jitsukawa, K.Kaneda : Chem Mater., 19, 1249-1256 (2007).
2Organic Square, 21, 2 (2007).
3, 71, 8 (2003).
OH
OHO
O OH
OH
OH
OH
OH10
7
OH
OH
NOH
SOH
Illustration of RuHAP- Fe2O3 and recovery from the reaction
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16
Hydroxyapatite-bound Ru Complex catalystRuHAP
[HAPCa10(PO4)6(OH)2] RuCl
1 1 2 2 3 2 4 3
No. ()
182-01851 1g 7,500 Ruthenium() Hydroxyapatite RuHAP
188-01853 5g 26,000
1K. Yamaguchi, K. Mori, T. Mizugaki, K. Ebitani, K. Kaneda : J. Am. Chem. Soc., 122, 7144 (2000).
2K. Mori, K. Yamaguchi, T. Mizugaki, K. Ebitani, K. Kaneda : Chem. Commun. 461 (2001).
3K. Mori, M. Tano, T. Mizugaki, K. Ebitani, K. Kaneda : New J. Chem., 1536 (2002).
N
CN RuHAP,N2,H2O
150, 24h N
NH2
O
conv. 100%yield >99%
RuHAP,O2
80, 2h
RuHAP,O2
80, 2h
OH CHO
OH O
conv. 100%yield >99%
conv. 100%yield 99%
RuHAP,O2
90, 4hHO
NH2HO
CN
yield >99%
conv. 100%yield 99%
RuHAP,O2
80, 3hSi
CH3
CH3
H Si
CH3
CH3
OH
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17
- Palladium- Hydrotalcite
(Mg6Al2(OH)16 CO34H2O) Pd(OAc)2(Py)2
Oxidation of Geraniol Recycling of Pd()-Hydrotalcite in the Oxidation of benzyl alcohol
entry catalyst gas time(h) number of use GLC yield(%) first 98 second 89 1a Pd()-Hydrotalcite O2 2 third 77 first 98
2b Pd()-Hydrotalcite air 3 second 90 first 96 second 97 3c Pd()-Hydrotalcite(m) O2 5 third 90
No. ()
Palladium()- Hydrotalcite Pd 1.5% 161-20543 5g 20,000
Palladium()- Hydrotalcite(m) Pd 0.8% 168-20553 10g 20,000
Pd 2
1 : , 69 (2), 10-12 (2001).
2T. Nishimura, N. Kakiuchi, S. Uemura : Chem. Commun., 1245 (2000).
3N. Kakiuchi, T. Nishimura, M. Inoue, S. Uemura : Bull. Chem. Soc. Jpn., 74, 165 (2001).
OH OPd-hydrotalcite
toluene/pyridineH
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18
MC ScOTf3
Sc
OTf3
MCScOTf3
ScOTf3
12
Imino Aldol Flow System Flow System Friedel-Crafts Batch System Batch System AzaDiels-Alder 3 Mannich Strecher Michael Diels-Alder
No. ()
Scandium Trifluoromethanesulfonate, Microencapsulated MC Sc(OTf)3 196-12041 1g 18,000
1 67, 6 (1999).
2S. Kobayashi, S. Nagayama : J. Am. Chem. Soc., 120, 2985 (1998).
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19
PMI ScOTf3 Polymer-Micelle-Incarcerated Scandium Trifluoromethanesulfonate
-
Mukaiyama Aldol Reaction
No. ()
PMI Scandium Trifluoromethanesulfonate PMI Sc (OTf)3 167-22821 1g 17,000
1M. Takeuchi, R. Akiyama, S. Kobayashi : J. Am. Chem. Soc., 127, 13096 (2005).
PI Pt Polymer-Incarcerated Platinum
Hydrogenation of Cholesterol
No. ()
PI Platinum PI Pt 163-22801 1g 23,000
1Y. Miyazaki, H. Hagio, S. Kobayashi : Org. Biomol. Chem., 4, 2529 (2006).
Ph H
O+ OMe
OSiMe3PMI Sc(OTf)3 (5mol%)
Ph
OH
OMe
O
CH2Cl2, rt, 3hr
PI Pt
OO
OO H
X Y Z
4 H2PtCl6 6H2Ocross-linking
130oC, 4hr
HSiEt3microencapsulation no solvent
yield 1st 2nd 3rd 92 96 94
H
H
HHO
H
H
HHO
H
H2, PI Pt (5mol%), 1atm
CH2Cl2, rt, 24hr yield : 80%
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20
PI Pd Polymer-Incarcerated Palladium
1 2 2 1 3 13
No. ()
168-21991 1g 8,000 Pl Pd (Pd abt.3%)
164-21993 5g 27,000
1R. Akiyama, S. Kobayashi: J. Am. Chem. Soc., 125, 3412 (2003).
2K. Okamoto, R. Akiyama, S. Kobayashi: Org. Lett., 6, 1987 (2004).
3K. Okamoto, R. Akiyama, S. Kobayashi: J. Org. Chem., 69, 2871 (2004).
B(OH)2Br +
PI Pd (5 mol%)P(o-MeOC6H4)3 (5 mol%)
K3PO4 (2.0 eq)toluene-H2O (4/1), reflux, 2 h
OCO2Me +CO2Me
CO2MeCO2Me
CO2Me
PI Pd (5 mol%)
THF, reflux, 2 h
PPh3 (5 mol%) Yield1st. 88 %5th. 98 %
O OPI Pd (5 mol%)H2 (1 atm)THF, rt, 1 h
Yield1st. 85%5th. 90%
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21
Pd EnCatTM
Pd5ppm20ppm - -Heck
Suzuki Reaction Heck Reaction Carbonylation Hydrogenation Stille Reaction Transfer hydrogenation
Pd Matrix No. ()
161-21481 1g 10,000
167-21483 5g 35,000 Pd EnCatTM 30 3.7-4.5% 30%
169-21482 25g
165-21521 1g 10,000
161-21523 5g 35,000 Pd EnCatTM 40 3.9-4.8% 40%
163-21522 25g
168-21491 1g 11,000
164-21493 5g 38,500 Pd EnCatTM TPP30 3.5-4.5% 30%
166-21492 25g
161-21501 1g 11,000
167-21503 5g 38,500 Pd EnCatTM TOTP30 4.2-5.1% 30%
169-21502 25g
161-21981 1g 12,000
167-21983 5g 40,000 Pd() EnCatTM BINAP30 3.7-5.0% 30%
169-21982 25g
164-21971 1g 6,000
160-21973 5g 23,000 Pd(0) EnCatTM 30NP
(wetted with ca.45%water) 1.8-2.8% 30%
162-21972 25g
Pd EnCatTM Reaxa
BrR' B(OH)2 R
RR'+
R I R CO 2 Bu
n
Br Ph
R R
R Br
R+
BrBr
O
OH
3
P
3
P
PPh2
PPh2
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22
PEG-PS ---
30
30
1
2
No. ()
Di--chlorobis[(-allyl)palladium()], Supported PEG-PS Resin Pd-PEP 043-27731 500mg 20,000
1Y. Uozumi , T. Watanabe : J. Org.Chem., 64, 6921 (1999).
2Y. Uozumi , H. Danjo , T. Hayashi : J. Org. Chem., 64, 3384 (1999).
I Pd-PEP (3 mol% Pd) ,CO (1 atm)
in H2O KOH or K2CO3, 25 oC
CO2HR R
R=H, 2- Me, 3-Me, 4-Me, 4-OMe, 4-NO2, 4-CF3, 3-CO2 Et, 4-Br, 4-Cl
I Pd-PEP (3 mol% Pd) , CO (1 atm)
in ROH K2CO3, 25 oC
CO2R
Yield R=Me 81%, R=Et 81%
XR1
R2
B(OH)2+ R2
R1Pd-PEP (2 mol% Pd)
in H2O, KOH , 25 oC , 24 h
X=Br, I : R1=H, Me : R2=H, Me, OMe Yield 66-91%
Run (R=H) 1-10th 11-20th 21-30th 1-30th
Yield(%) ave.98 ave.98 ave.98 ave.97
-
23
Nanocage, Nanobowl
Pd-Nanocage1-4Pd-Nanobowl5,6
Pt-Nanocage7
Pt-Nanocage
Pd-Nanocage Pd-Nanobowl Pt-Nanocage [(en)Pd](ONO2)2
Diels-Alder Wacker [2+2]
No. ()
Palladium-Nanocage - 160-20471 1g 23,000
165-21761 200mg 10,000 Palladium-Nanobowl -
161-21763 1g 35,000
052-07341 200mg 8,000 (Ethylenediamine)dinitratopalladium () [(en)Pd](ONO2)2
058-07343 1g 30,000
161-21741 100mg 12,000 Platinum-Nanocage -
167-21743 500mg 45,000
-
24
1D. Oguro, M. Miyazawa, H. Oka, K. Yamaguchi, K. Ogura, M. Fujita : Nature, 378, 469 (1995).
2T. Kusukawa, M. Fujita : Angew. Chem., Int. Ed. Engl., 37, 3142 (1998).
3H. Ito, T. Kusukawa, M. Fujita : Chem. Lett., 598 (2000).
4M. Yoshizawa, Y. Takeyama, T. Okano, M. Fujita : J. Am. Chem. Soc., 125, 3243 (2003).
5M. Fujita, S.-Y. Yu, T. Kusukawa, H. Fumaki, K. Ogura, K. Yamaguchi : Angew. Chem., Int. Ed. Engl., 37, 2082 (1998).
6S.-Y. Yu, T. Kusukawa, K. Biradha, M. Fujita : J. Am. Chem. Soc., 122, 2665 (2000).
7F. Ibukuro, T. Kusukawa, M. Fujita : J. Am. Chem. Soc., 120, 8561 (1998).
NiCo
60m
No. ()Dibromobis(triphenylphosphine)nickel(), Supported PS Resin PS ()()
042-28421 500mg 18,000
Dichlorobis(triphenylphosphine)cobalt(), Supported PS Resin PS ()()
049-28431 500mg 18,000
No.042-28421
No.049-28431
-
25
(R)-3-I-ZrMS
MS
storage time,week 0 2 6 13
Yield(%) quant. quant. quant. quant.
syn/anti 5/95 5/95 5/95 5/95
ee,%(anti) 99 99 99 99 -*
No. ()
097-05271 1g 15,000 (R)-3-l-ZrMS
093-05273 5g 55,000
1S. Kobayashi, S. Saito, M. Ueno, Y. Yamashita : Chem. Commun., 2016 (2003).
2S. Kobayashi, M. Ueno, S. Saito, Y. Mizuki, H. Ishitani, Y. Yamashita: Proc. Natl. Acad. Sci. USA, 101, 5476 (2004).
-
26
(+)(-)-NMI2ZrCl2 ZACA
ZACA Vitamin EVitamin KPhytol
Zr-Catalyzed Asymmetric Carboalumination of Alkenes Styrene-based protocol for the synthesis of ,-diheterofunctional deoxypolypropionates1 ZACA-lipase-catalyzed acetylation2
No. ()
025-15981 200mg 8,000 (-)-Bis[1-{(1'S,2'S,5'R)-2'-isopropyl-5'-methylcyclohexyl}indenyl] zirconium() Dichloride
(-)-(NMI) 2ZrCl 2 021-15983 1g 28,000
022-16111 200mg 8,000 (+)-Bis[1-{(1'S,2'S,5'R)-2'-isopropyl-5'-methylcyclohexyl}indenyl] zirconium() Dichloride
(+)-(NMI) 2ZrCl 2 028-16113 1g 28,000
1T. Novak, Z. Tan, B. Liang, E. Negishi : J. Am. Chem. Soc., 127, 2838 (2005).
2Z. Huang, Z. Tan, T. Novak, G. Zhu, E. Negishi : Adv. Synth. Catal., 349. 539 (2007).
dr
Zr ClCl
(-)-(NMI)2ZrCl2
-
27
Methanethiolate-Bridged Diruthenium Complex(met-DIRUX) 2
met-DIRUX 89 met-DIRUX-OTf 89RuCl3
pentamethylcyclopentadiene methanethiol
2
met-DIRUX
1
23
4
5 6
met-DIRUX-OTf
7
1 23 2 4
No. ()
met-DIRUX 130-14581 200mg 13,000
met-DIRUX-OTf 132-14781 200mg 18,000
1Y. Nishibayashi, M. Yamanashi, I. Wakiji, M. Hidai : Angew. Chem. Int. Ed., 39, 2909 (2000).
2Y. Nishibayashi, M. Yamanashi, I. Wakiji, M. Hidai : J. Am. Chem. Soc., 122, 11019 (2000).
3Y. Nishibayashi, I. Wakiji, Y. Ishii, S. Uemura, M. Hidai : J. Am. Chem. Soc., 123, 3393 (2001).
4Y. Nishibayashi, Y. Inada, M. Hidai, S. Uemura : J. Am. Chem. Soc., 124, 7900 (2002).
5Y. Nishibayashi, M. Yoshikawa, Y. Inada, M. Hidai, S. Uemura : J. Am. Chem. Soc., 124, 11846 (2002).
6Y. Nishibayashi, Y. Inada, M. Hidai, S. Uemura : J. Am. Chem. Soc., 125, 6060 (2003).
7Y. Nishibayashi, Y. Inada, M. Yoshikawa, M. Hidai, S. Uemura : Angew. Chem. Int. Ed., 42, 1495 (2003).
8Y. Nishibayashi, M. Hidai, S. Uemura : Organic Square, 13, 1 (2004).
9Y. Nishibayashi, M. D. Milton,Y. Inada, M. Yoshikawa, I. Wakiji, M. Hidai, S. Uemura : Chem. Eur. J., 11, 1433 (2005).
Ru
Ru
SS
H3CCH3
Cl
ClRu
Ru
SS
H3CCH3
H2O
Cl
OTf
OR
Ph
SR'
Ph
NHAr
Ph
P(O)Ph2
Ph
Ph
O
R'SH (R'= alkyl, Ph)
60 oC, 4 h
OH
Ph + met-DIRUX (5 mol%) NH4BF4 (10 mol%)
ROH (R= Me, Et, Ph)
60 oC, 15 min
ArNH2
60 oC, 4 h
HP(O)Ph260 oC, 1 h
acetone
reflux, 3 h
yield: 63-91%
yield: 46-86%
yield: 64-93%
yield: 56%
yield: 85%
OH
PhPh
O
PhPh
O+
ClCH2CH2Cl 60 oC, 1 h
met-DIRUX-OTf (5 mol%)
yield: 88%
met-DIRUX met-DIRUX-OTf
met-DIRUX OTf[Cp*RuCl(2-SMe) 2 RuCp*(OH2)]OTfmet-DIRUX[Cp*RuCl(2-SMe) 2 RuCp*Cl] Cp*5-C5Me5
-
28
Ru Umicore
-
Umicore M1
Grubbs Umicore M1RCM
1
RCM 2
98
97
94
97
87
Umicore M2 Grubbs Umicore M2
3
RCM
No. ()
213-01371 1g 10,000 Umicore M1
219-01373 5g 40,000
210-01381 100mg 9,000 Umicore M2
216-01383 500mg 29,000
1A.Frstner, et al.: Chem. Eur.J., 4811, 7 (2001).
2A.Frstner, et al.: Chem. Eur.J., 320, 9 (2003).
3A.Frstner, et al.: J.Org.Chem., 65, 2204 (2000).
Dichloro(3-phenyl-1H-inden-1-ylidene)bis-(tricyclohexylphosphine)ruthenium()
Dichloro(3-phenyl-1H-inden-1-ylidene)[1,3-bis(2,4,6-trimethyl-phenyl)-2-imidazolidinylidene](tricyclohexylphoshine) ruthenium()
-
29
Nafion Dispersion Solution
Nafion Perfluorosulfonic Acid/PTFE copolymerH+
5, 10, 20
Nafion
DE520 DE521 DE1020 DE1021 DE2020 DE2021
min. 5.0 min. 5.0 min.10.0 min.10.0 min.20.0 min.20.0 Polymer Content (%)
max. 5.4 max. 5.4 max.12.0 max.12.0 max.22.0 max.22.0
Water Content (%) 453 453 87~90 87~90 342 342
VOC Content (%) 503 503 1 1 462 462
1-Propanol 483 483 442 442
Ethanol 4 4 2 2
Mixed Ethers and Other VOCs 1 1 1 1
Specific Gravity 0.92 - 0.94 0.92 - 0.94 1.05 - 1.07 1.05 - 1.07 0.97 - 0.99 0.97 - 0.99
Available Acid Capacity (meq/g. H+ polymer basis) 1.00 0.92 1.00 0.92 1.00 0.92
Viscosity (cP:at 25 and 40sec-1 Shear Rate) 1040 1040 210 210 50500 50500
No. ()
320-86712 25ml 10,000 5% Nafion Dispersion Solution DE520 CS type
328-86713 100ml 30,000
323-86702 25ml 8,000 5% Nafion Dispersion Solution DE521 CS type
321-86703 100ml 24,000
323-46402 25ml 14,000 10% Nafion Dispersion Solution DE1020
321-46403 100ml 42,000
327-86722 25ml 12,000 10% Nafion Dispersion Solution DE1021 CS type
325-86723 100ml 36,000
324-86732 25ml 18,000 20% Nafion Dispersion Solution DE2020 CS type
322-86733 100ml 54,000
323-87422 25ml 16,000 20% Nafion Dispersion Solution DE2021 CS type
321-87423 100ml 48,000
CS type:Chemical Stability Nafion[]
NR-50 Nafion NR-50
No. ()
144-05991 5g 7,000 Nafion NR-50
142-05992 25g 21,500
Nafion Perfluorinated Ion-exchange Resin
-
30
Au
CAS No. No. ()
Ammonium Tetrachloroaurate() n-Hydrate
NH4(AuCl4)nH2O 13874-04-9 - 321-49921 1g 15,000 -
Chloro(triethylphosphine)gold () [AuCl{P(C2H5)3}]=350.58 15529-90-5 034-15491 1g 15,700
Chloro(triphenylphosphine)gold() [AuCl{P(C6H5)3}]=494.71 14243-64-2 037-15481 1g 15,700
Co
CAS No. No. ()
Bis(pentamethylcyclopentadienyl)- cobalt() Hexafluorophosphate
C20H30CoPF6 =474.35 79973-42-5 - 324-86271 1g 10,000
57-2PRTR1
Cobalt, Powder, - 45m, 99.5% Co=58.933 7440-48-4 - 030-18271 100g 12,500 57-2PRTR1 039-20272 25g 2,500Cobalt, Lump
Co=58.933 7440-48-4 - 033-20275 500g 18,000
57-2PRTR1
Cobalt, Sponge, 99.99% Co=58.933 7440-48-4 - 036-06801 10g 18,000 57-2PRTR1 033-20172 25g 7,000Cobalt() Acetate
Co(CH3COO)2=177.02 71-48-7 - 035-20171 100g 21,000
57-2PRTR1
030-03602 25g 1,800 032-03601 100g 4,000Cobalt() Acetate Tetrahydrate
Co(CH3COO)24H2O=249.08 6147-53-1
034-03605 500g 8,400
57-2PRTR1
Cobalt() Bromide CoBr2=218.74 7789-43-7 - 034-07022 25g 12,000 57-2PRTR1
039-03672 25g 1,750Cobalt() Carbonate Basic
CoCO3=118.94 513-79-1 Pr. G. 033-03675 500g 13,000 57-2PRTR1
035-10982 25g 2,800Cobalt() Chloride
CoCl2=129.84 7646-79-9 039-10985 500g 15,500 57-2PRTR1
Cobalt() Chloride Hexahydrate, 99.5%
CoCl26H2O =237.93 7791-13-1 - 035-12822 25g 3,300
57-2PRTR1
Cobalt() Chromate Dihydrate CoCrO42H2O=210.96 13455-25-9 Pr. G. 030-03722 25g 2,900
57-2PRTR1-- 2
032-06842 25g 2,400Cobalt Hydroxide
H2CoO2=92.95 21041-93-0 - 036-06845 500g 18,000 57-2PRTR1
034-12831 50g 3,200Cobalt() Nitrate Hexahydrate, 99.5%
Co(NO3)26H2O=291.03 10026-22-9 - 036-12835 500g 13,000
57-2PRTR1
035-05651 100g 5,500Cobalt() Oxide
CoO=74.93 1307-96-6 - 037-05655 500g 20,500
57-2PRTR1
Cobalt(,) Oxide,1.70-3.35mm (6-10mesh) Co3O4=240.80 1308-06-1 038-09002 25g 4,600
57-2PRTR1
Cobalt(,) Oxide, 0.85-2.36mm (8-20mesh) Co3O4=240.80 1308-06-1 035-09012 25g 4,200
57-2PRTR1
039-03792 25g 2,800Cobalt() Phosphate Octahydrate
Co3(PO4)28H2O=510.86 10294-50-5 - 033-03795 500g 17,600
57-2PRTR1
030-07242 25g 3,200Cobalt() Stearate
Co(C18H35O2)2 =625.88 13586-84-0 Pr. G. 034-07245 500g 17,000
57-2PRTR1
Cobalt() Sulfate Heptahydrate, 99.5%
CoSO47H2O =281.10 10026-24-1 - 039-12842 25g 3,700
57-2PRTR1
Cobalt() Sulfide CoS=91.00 1317-42-6 - 036-03822 25g 8,200 57-2PRTR1
Dibromobis(triphenylphosphine)- cobalt()
[(C6H5)3P]2CoBr2 =743.32 14126-32-0 - 358-05572 25g 9,000
57-2PRTR1
Dichlorobis(triphenylphosphine)cobalt (), Supported PS Resin
- - 049-28431 500mg 18,000
082-07361 10g 4,200Hexaamminecobalt() Chloride
Cl3CoH18N6 =267.47 10534-89-1 080-07362 25g 8,500
57-2PRTR1
2,3,7,8,12,13,17,18-Octaethylporphy- rinato Cobalt()
C36H44CoN4 =591.71 17632-19-8 - 159-01461 250mg 42,000
57-2PRTR1
Raney Cobalt (about 48%) - - - 189-00462 25g 3,500 57-2PRTR1
P
2
CoBr2
P
2
CoBr2
n
N
N N
NCo
-
31
CAS No. No.
()
(Tetraaminochlorophthalocyaninato) -cobalt()
[Co(C32H19ClN12)]=665.97 - - 208-10791 500mg 41,000
57-2PRTR1
(Tetra-t-butylphthalocyaninato)cobalt ()
[Co(C48H48N8)] =795.90 129551-41-3 - 202-10571 500mg 33,600
57-2PRTR1
(Tetracarboxyphthalocyaninato)cobalt ()
[Co(C36H16N8O8)]=747.51 25511-95-9 - 208-10671 500mg 24,000
57-2PRTR1
5,10,15,20-Tetraphenylporphyrinato Cobalt()
C44H28CoN4 =671.67 14172-90-8 - 204-09661 1g 27,000
57-2PRTR1
323-86241 1g 8,000Tris(2,2,6,6-tetramethyl-3,5-heptane- dionato)cobalt()
C33H57CoO6 =608.74 14877-41-9 - 329-86243 5g 28,000
57-2PRTR1
Ir
CAS No. No. ()
Ammonium Hexachloroiridate() (NH4)2IrCl6=441.01 16940-92-4 012-15691 1g 14,500 039-14341 1g 15,700 Carbonylchlorobis(triphenylphosphine)
iridium()
C37H30ClIrOP2 =780.25 14871-41-1
035-14343 5g 52,000
Di--chlorobis[(-cycloocta-1,5- diene)iridium ()]
[Ir2Cl2(C8H12)2] =671.71 12112-67-3 045-24251 1g 18,900
Iridium, Powder, - 45m Ir=192.22 7439-88-5 - 097-04811 1g 18,000 Iridium() Chloride IrCl3=298.57 10025-83-9 - 096-01601 1g 11,000 Iridium() Chloride, 99.5% IrCl4=334.01 10025-97-5 - 092-02921 1g 11,200 Iridium() Oxide IrO2=224.22 12030-49-8 Pr. G. 097-03571 1g 12,000 Potassium Hexachloroiridate() n -Hydrate
K3[IrCl6]nH2O =522.23 (as anhyd.) 14024-41-0 164-16841 1g 25,000
Potassium Hexachloroiridate() K2[IrCl6]=483.13 16920-56-2 163-16671 1g 14,500 Sodium Hexachloroiridate() n -Hydrate
Na3[IrCl6]nH2O =473.90 (as anhyd.) 123334-23-6 196-10961 1g 12,600
Sodium Hexachloroiridate() n -Hydrate
Na2[IrCl6]nH2O =450.91 (as anhyd.) 19567-78-3 193-10971 1g 12,600
Tris(acetylacetonato)iridium() C15H21O6Ir=489.54 15635-87-7 - 326-37761 500mg 20,000
Ni
CAS No. No. ()
Ammonium Nickel() Sulfate Hexa- hydrate, 99.9%
(NH4)2Ni(SO4)26H2O=394.99
15699-18-0 - 015-12222 25g 2,700 57-2PRTR1
Bis[1,2-bis(butylthio)-1,2-ethenedi- thiolato]nickel()
[Ni(C10H18S4)2] =591.73 90157-73-6 - 024-11811 1g 16,800
57-2PRTR1
326-78041 1g 10,000Bis(1,5-cyclooctadiene)nickel(0)
C16H24Ni=275.06 1295-35-8 - 322-78043 5g 23,000 57-2PRTR1
327-80661 5g 8,000[1,3-Bis(diphenylphosphino)propane]- dichloronickel()
C27H26Cl2NiP2 =542.04 15629-92-2 - 325-80662 25g 30,000
57-2PRTR1
Bis(methylcyclopentadienyl)nickel() C12H14Ni=216.93 1293-95-4 - 322-86211 1g 12,000 57-2PRTR1
Bis(pentamethylcyclopentadienyl)- nickel() C20H30Ni=329.15 74507-63-4 - 321-85201 1g 15,000
57-2PRTR1
Bis(tetramethylcyclopentadienyl)nickel() C18H26Ni=301.09 79019-60-6 - 329-86341 1g 15,000
57-2PRTR1
325-27961 1g 8,000Chloro(cyclopentadienyl)(triphenyl- phosphine)nickel()
C23H2OClNiP =421.53 31904-79-7 - 321-27963 5g 29,000
57-2PRTR1
329-85241 5g 5,000Dibromobis(triphenylphosphine)nickel ()
C36H30Br2NiP2 =743.07 14126-37-5 - 327-85242 25g 15,000
57-2PRTR1
Dibromobis(triphenylphosphine)nickel (), Supported PS Resin
- - 042-28421 500mg 18,000 57-2PRTR1
N
N N
N
N
N
N
NCo Cl
NH2H2N
H2N NH2
N
N N
NCo
P
2
Ir(CO)Cl
Ir
Cl
Ir
Cl
S
S
S
S
S
SNi
S
S
P
2
NiBr2n
-
32
CAS No. No.
()
045-27551 5g 8,000Dichloro[1,2-bis(diphenylphosphino)-
ethane]nickel()
[(C6H5)2PCH2CH2P (C6H5)2]NiCl2=528.02
14647-23-5 - 043-27552 25g 26,000
57-2PRTR1
327-82822 25g 7,000Dichlorobis(triphenylphosphine)nickel ()
C36H30Cl2NiP2 =654.17 14264-16-5 - 325-82823 100g 21,000
57-2PRTR1
140-07252 25g 3,600 142-07251 100g 5,000Nickel, Beads, 99.9%
Ni=58.69 7440-02-0 - 144-07255 500g 9,500
57-2PRTR1
145-00982 25g 2,200Nickel, Powder, through 150m (100mesh)
Ni=58.69 7440-02-0 - 149-00985 500g 13,000
57-2PRTR1
Nickel, Sponge, 99.95% Ni=58.69 7440-02-0 - 148-03392 25g 21,000 57-2PRTR1 142-05752 25g 2,100Nickel() Acetate Tetrahydrate, 99.9%
(CH3COO)2Ni4H2O=248.84
6018-89-9 - 144-05751 100g 6,300
57-2PRTR1
Nickel() Amidosulfate Tetrahydrate (H2NSO3)2Ni4H2O=322.92 305808-25-7 149-05485 500g 3,700 57-2PRTR1
141-03402 25g 1,600Nickel() Bromide, Anhydrous
NiBr2=218.51 13462-88-9 - 145-03405 500g 8,700 57-2PRTR1
Nickel() Carbonate Basic CH4Ni3O74H2O=376.18 39430-27-8 - 144-01035 500g 4,100 57-2PRTR1
141-01062 25g 2,200Nickel() Chloride
NiCl2=129.60 7718-54-9 145-01065 500g 13,000 57-2PRTR1
Nickel() Chloride Hexahydrate, 99.9%
NiCl26H2O =237.69 7791-20-0 - 149-05343 50g 4,000
57-2PRTR1
Nickel() Fluoride Tetrahydrate NiF24H2O=168.75 13940-83-5 - 143-07122 25g 3,600 57-2
PRTR 1 148-01072 25g 2,300Nickel() Formate Dihydrate
(HCOO)2Ni2H2O=184.76 3349-06-2 - 142-01075 500g 7,200
57-2PRTR1
144-05572 25g 1,600Nickel() Hydroxide
Ni(OH)2=92.71 12054-48-7 Pr. G. 148-05575 500g 8,000 57-2PRTR1
Nickel() Nitrate Hexahydrate, 99.9% Ni(NO3)26H2O=290.79 13478-00-7 - 140-05351 100g 4,000 57-2PRTR1
Nickel() Oxide, 99.9% NiO=74.69 1313-99-1 - 143-05363 50g 4,000 57-2PRTR1 147-01162 25g 2,100Nickel() Potassium Cyanide Mono-
hydrate Ni(CN)22KCN
H2O=258.99 14220-17-8 Pr. G.
141-01165 500g 7,500
57-2PRTR1-
144-01172 25g 1,800 146-01171 100g 2,300Nickel() Sulfate Hexahydrate
NiSO46H2O =262.85 10101-97-0
148-01175 500g 3,300
57-2PRTR1
Nickel() Sulfate Hexahydrate, 99.9% NiSO46H2O =262.85 10101-97-0 - 144-05371 100g 2,500 57-2PRTR1
(Phthalocyaninato)nickel()
[Ni(C32H16N8)] =571.22 14055-02-8 - 163-14231 1g 24,000
57-2PRTR1
187-00022 25g 1,800Raney Nickel, about 50%
- 7440-02-0 Pr. G. 181-00025 500g 6,600
57-2PRTR1
Os
CAS No. No. ()
153-00401 100mg 4,400 159-00403 500mg 7,800Osmium() Oxide
OsO4=254.23 20816-12-0 157-00404 1g 10,800
57-2
153-02581 5g 13,000Osmium Oxide, Immobilized Catalyst I
OsO4=254.23 20816-12-0 151-02582 25g 50,000 57-2
Osmium() Oxide, Microencapsulated OsO4=254.23 20816-12-0 153-02081 1g 15,000 57-2Osmium() Oxide, PEM-Microen- capsulated OsO4=254.23 20816-12-0 158-02411 1g 20,000 57-2
Osmium, Powder Os=190.23 7440-04-2 - 501-22261 1g 27,800 Potassium Hexachloroosmate() Cl6K2Os=481.14 16871-60-6 - 324-40991 250mg 18,000
PP
NiCl Cl
N
N N
N
N
N
N
NNi
-
33
Pd
CAS No. No. ()
Ammonium Hexachloropalladate() (NH4)2[PdCl6] =355.21 19168-23-1 015-15681 1g 5,000
Ammonium Tetrachloropalladate() (NH4)2[PdCl4] =284.31 13820-40-1 015-15701 1g 12,000
Bis(acetonitrile)dichloropalladium () [PdCl2(CH3CN)2]=259.43 14592-56-4 024-12151 1g 9,000 -
Bis(acetylacetonato)palladium()
Pd(C5H7O2)2 =304.62 14024-61-4 026-10891 1g 11,000
Bis(benzonitrile)dichloropalladium()
Cl2Pd(C7H5N)2 =383.57 14220-64-5 027-12141 1g 9,000 -
Bis(dibenzylideneacetone)palladium (0)
C34H28O2Pd =575.00 32005-36-0 - 329-42021 1g 8,000
320-94201 1g 9,500[1,2-Bis(diphenylphosphino)ethane]- dichloropalladium()
C26H24Cl2P2Pd = 575.74 19978-61-1 - 326-94203 5g 35,000
327-94211 1g 10,000[1,1-Bis(diphenylphosphino)ferrocene]- dichloropalladium()
C34H28Cl2FeP2Pd= 731.70 72287-26-4 - 323-94213 5g 35,000
324-98741 1g 7,000[1,1'-Bis(diphenylphosphino)ferrocene]di- chloropalladium(), Dichloromethane
Adduct
C34H28Cl2FeP2Pd=816.64 95464-05-4 -
320-98743 5g 24,000
Bis(ethylenediamine)palladium() Chloride
[(NH2CH2CH2NH2)2Pd]Cl2=297.52
13963-53-6 - 329-37751 500mg 15,000
354-11081 100mg 7,000Bis(tri-t-butylphosphine)palladium(0)
C24H54P2Pd = 511.05 53199-31-8 - 350-11083 500mg 18,000
Diamminedichloropalladium() H6Cl2N2Pd=211.39 14323-43-4 - 323-40961 500mg 15,000
Di--chlorobis[(-allyl) palladium()], Supported PEG-PS Resin
- - 043-27731 500mg 20,000
327-94191 1g 9,500trans-Dichlorobis(tricyclohexylphos- phine)palladium()
C36H66Cl2P2Pd = 738.18 29934-17-6 - 323-94193 5g 35,000
040-22481 1g 4,700 046-22483 5g 15,000
trans -Dichlorobis(triphenylphosphine)palladium()
C36H30Cl2P2Pd =701.91 13965-03-2
048-22482 25g
Dichloro(-cycloocta-1,5-diene)palla- dium()
[PdCl2(C8H12)] =285.51 12107-56-1 040-24061 1g 14,000
052-07341 200mg 8,000(Ethylenediamine)dinitratopalladium ()
C2H8N4O6Pd =290.53 63994-76-3 058-07343 1g 30,000
Palladium, Flake, 99.9% Pd=106.42 7440-05-3 - 165-20421 2g 30,000 2- 163-07141 1g 5,600 169-07143 5g 21,000Palladium() Acetate
Pd(OOCCH3)2 =224.51 3375-31-3
161-07142 25g 93,000
163-07543 5g 3,600 165-07542 25g 13,000Palladium-Activated Carbon (Pd 5%)
- - - 167-07541 100g 40,000
2-
161-15273 5g 4,200 163-15272 25g 12,000Palladium-Activated Carbon (Pd 10%)
- - 165-15271 100g 40,000
2-
163-21441 1g 4,000 169-21443 5g 13,500
Palladium-Activated Carbon Ethylene- diamine Complex (Pd 3.5~6.5%)
- -
161-21442 25g 46,000
57-2PRTR1
167-23301 1g 5,000 Palladium-Activated Carbon Ethylene- diamine Complex (Pd 8.5~11.5%)
- - 163-23303 5g 16,000 57-2PRTR1
Palladium-Alumina Pd=106.42 7440-05-3 163-13871 10g 10,500
Palladium Asbestos abt.10% - - - 162-00031 1g 3,500
57-2PRTR1
Palladium Asbestos abt.20% - - - 165-00021 1g 4,500
57-2PRTR1
Palladium Asbestos abt.30% - - - 168-00011 1g 7,400
57-2PRTR1
Palladium-Barium Carbonate(Pd 5) - - 160-13881 10g 8,000 Palladium-Barium Sulfate (Pd 5%) - - 167-13891 10g 10,000 Palladium Black Pd=106.42 7440-05-3 - 169-00041 1g 12,500 Palladium() Bromide PdBr2=266.23 13444-94-5 - 322-37741 1g 16,000 Palladium() Chloride, 99.9% PdCl2=177.33 7647-10-1 - 168-13561 1g 6,300
167-22181 1g 4,500Palladium-Fibroin
- - 163-22183 5g 14,000
N PdCl22
OPdO
FeP
PPd
Cl
ClCH2Cl2
Pd
Cl
Cl
-
34
CAS No. No.
()
Palladium ()-Hydrotalcite (Pd 1.5%) - - 161-20543 5g 20,000 Palladium ()-Hydrotalcite(m) (Pd 0.8 %) - - 168-20553 10g 20,000
165-21761 200mg 10,000Palladium-Nanobowl
C84H96N48O36Pd6 =2,992.48 213113-25-8
161-21763 1g 35,000
Palladium-Nanocage
C84H96N48O36Pd6 =2,992.48 - 160-20471 1g 23,000
Palladium() Nitrate, 99.9% Pd(NO3)2=230.43 10102-05-3 - 165-13451 1g 7,200 1- 324-81651 5g 3,500 5%Palladium on Activated Carbon,
Degussa type E 101 NE/W 5%Pd -
322-81652 25g 11,000 351-13051 5g 3,500 5%Palladium on Activated Carbon,
Degussa type E 105 NN/W 5%Pd -
359-13052 25g 11,000 355-13071 5g 3,500 5%Palladium on Activated Carbon,
Degussa type E 105 O/W 5%Pd -
353-13072 25g 11,000 358-13061 5g 3,500 5%Palladium on Activated Carbon,
Degussa type E 106 R/W 5%Pd -
356-13062 25g 11,000 162-15281 1g 7,800Palladium() Oxide
PdO=122.42 1314-08-5 168-15283 5g 27,500
161-22221 1g 8,000Palladium-Polyethyleneimine
- - 167-22223 5g 26,000
4-4-
Palladium() Sodium Chloride Trihy- drate
PdCl22NaCl3H2O=348.26
13820-53-6 167-00081 1g 5,800
166-14961 1g 9,300Palladium() Sulfate
PdSO4=202.48 13566-03-5 164-14962 25g 68,000
168-21991 1g 8,000PI Palladium (Pd abt. 3%)
- - 164-21993 5g 27,000
Potassium Hexachloropalladate() K2(PdCl6)=397.33 16919-73-6 164-17681 1g 14,000 Potassium Tetrachloropalladate() K2(PdCl4)=326.43 10025-98-6 160-17661 1g 13,000
Tetraamminepalladium() Chloride Pd(NH3)4Cl2 =245.42 13815-17-3 - 325-37731 100mg 7,000
Tetraamminepalladium() Nitrate Solution (abt.13%)
(NH3)4Pd(NO3)2 =298.55 13601-08-6 - 320-40971 5g 15,000
Tetrakis(acetonitrile)palladium() Bis (tetrafluoroborate)
Pd(CH3CN)4(BF4)2=444.24 21797-13-7 - 201-14701 1g 22,000
-PRTR1
209-14643 1g 5,000Tetrakis(triphenylphosphine)palladium (0)
C72H60P4Pd =1155.58 14221-01-3 Pr. G. 203-14641 5g 16,000
Pt
CAS No. No. ()
Ammonium Hexachloroplatinate() (NH4)2[PtCl6] =443.87 16919-58-7 018-15671 1g 12,400 57-2
Ammonium Tetrachloroplatinate() (NH4)2[PtCl4] =372.97 13820-41-2 011-15661 1g 12,500 57-2
Bis(acetylacetonato)platinum()
[Pt(C5H7O2)2] =393.30 15170-57-7 027-12021 1g 15,700 57-2
Di--chlorobis[chloro(cyclohexene)- platinum()]
C12H20Cl4Pt2 =696.26 12176-53-3 - 326-40951 500mg 25,000
047-22511 1g 16,000cis -Diamminedichloroplatinum()
Pt(NH3)2Cl2 =300.05 15663-27-1 043-22513 5g 58,000
57-2
044-22521 1g 14,000trans -Diamminedichloroplatinum()
Pt(NH3)2Cl2 =300.05 14913-33-8 040-22523 5g 52,000
57-2
040-22501 1g 10,500cis -Dichlorobis(triphenylphosphine)- platinum()
[PtCl2{P(C6H5)3}2]=790.57 15604-36-1 046-22503 5g 36,500
Dichloro(-cycloocta-1,5-diene)plati- num()
[PtCl2(C8H12)] =374.17 12080-32-9 044-24081 1g 16,500 57-2
Hydrogen Hexachloroplatinate() Hexahydrate, 99.9%
H2Cl6Pt6H2O=517.90 18497-13-7 - 089-05311 1g 9,800 57-2
Hydrogen Hexahydroxoplatinate() H2[Pt(OH)6] =299.14 51850-20-5 - 322-43111 500mg 15,000
PI Platinum - - 163-22801 1g 23,000 Platinum-Activated Carbon (Pt 5%) - 7440-06-4 167-13911 10g 11,200 57-2Platinum-Alumina (Pt 5%) - - 168-13941 10g 16,000 57-2
Platinum Asbestos (Pt 10%) - - 165-12111 1g 4,200
57-2PRTR1
Platinum Asbestos (Pt 20%) - - 168-12101 1g 6,500
57-2PRTR1
Pt
Cl
Cl
-
35
CAS No. No.
()
Platinum() Barium Cyanide Tetra- hydrate
PtBa(CN)44H2O=508.56
- - 165-02841 1g 20,500 57-2PRTR1-
Platinum Black Pt=195.08 7440-06-4 Pr. G. 168-11121 1g 18,000 57-2Platinum-Calcium Carbonate (Pt 5%) - - 164-13921 10g 8,900 Platinum() Chloride PtCl2=265.99 10025-65-7 166-15821 1g 12,500 Platinum() Chloride PtCl4=336.89 13454-96-1 - 324-37701 500mg 12,500 57-2
167-22701 1g 4,000Platinum, Immobilized Catalyst I
- - 163-22703 5g 12,000
161-21741 100mg 12,000Platinum-Nanocage
- - 167-21743 500mg 45,000
Platinum() Oxide PtO2=227.09 1314-15-4 - 169-08341 1g 15,000 326-49351 1g 4,500Platinum(0)-2,4,6,8-tetramethyl-2,4,6,8- tetravinylcyclotetrasiloxane Complex
(Pt1.7)
[(C24H48O4Si4)y]Ptx 68585-32-0 - 322-49353 5g 13,000
4-3-
Potassium Hexachloroplatinate() K2PtCl6=485.99 16921-30-5 163-02881 1g 10,500 57-2Potassium Hexahydroxoplatinate() H6K2O6Pt=375.32 12285-90-4 - 328-37721 500mg 15,000
166-12901 1g 9,500Potassium Tetrachloroplatinate()
K2(PtCl4) =415.09 10025-99-7 162-12903 10g 72,000
57-2
Potassium Tetranitroplatinate() K2[Pt(NO2)4] =457.30 13815-39-9 - 326-43371 1g 20,000 5- 57-2
Tetraammineplatinum() Chloride n -Hydrate
Cl2H12N4Pt=334.11(as anhyd. ) 13933-32-9 200-12711 1g 15,700 57-2
Tetraammineplatinum() Hydrogen- carbonate
Pt(NH3)4(HCO3)2 =385.23 123439-82-7 - 321-37711 500mg 15,000
Tetraammineplatinum() Hydroxide Solution(abt.15)
[Pt(NH3)4] (OH)2=297.21 38201-97-7 - 323-41321 500mg 15,000 57-2
Tetrakis(triphenylphosphine)platinum (0)
[Pt{P(C6H5)3}4]=1,244.24 14221-02-4 202-12771 1g 12,000 57-2
Rh
CAS No. No. ()
322-32741 100mg 8,000(Acetylacetonato)carbonyl(triphenyl- phosphine)rhodium()
Rh(C5H7O2)(CO)[P(C6H5)3]=492.31
25470-96-6 - 328-32743 500mg 20,000
57-2
(Acetylacetonato)(-cycloocta-1,5- diene)rhodium()
[Rh(C5H7O2) (C8H12)]=310.20
12245-39-5 014-14551 1g 26,000 57-2
(Acetylacetonato)dicarbonylrhodium ()
[Rh(C5H7O2)(CO)2]=258.04 14874-82-9 011-14561 1g 43,000 57-2
Ammonium Hexachlororhodate() n -Hydrate
(NH4)2[RhCl6]nH2O=369.74 (as anhyd.) 15336-18-2 014-15651 1g 29,000 57-2
036-14351 1g 13,700Carbonylhydridotris(triphenylphos-
phine)rhodium()
C55H46OP3Rh =918.80 17185-29-4
032-14353 5g 52,500 57-2
035-15921 100mg 3,200Chlorocarbonylbis(triphenylphosphine)-
rhodium()
[(C6H5)3P]2Rh(CO)Cl=690.95 13938-94-8
031-15923 1g 16,800 57-2
034-14271 1g 14,500Chlorotris(triphenylphosphine)rhodium()
C54H45ClP3Rh =925.23 14694-95-2 030-14273 5g 52,000
57-2
Di--chlorobis[(-cycloocta-1,5-diene)- rhodium()]
[Rh2Cl2(C8H12)2]=493.08 12092-47-6 047-24071 1g 65,000 57-2
Dodecacarbonyltetrarhodium (0) [Rh4(CO)12] =747.75 19584-30-6 041-24231 1g 36,700 3- 57-2
Hexadecacarbonylhexarhodium (0) [Rh6(CO)16] =1,065.60 28407-51-4 084-06841 1g 26,000 57-2
Rhodium,Powder,99.9% Rh=102.91 7440-16-6 - 186-00151 1g 60,000 57-2Rhodium Acetate Hydrate Rh(C2H4O2)xH2O 42204-14-8 - 329-41421 500mg 15,000 57-2
180-01151 250mg 13,500Rhodium() Acetate, Dimer Dihydrate
[Rh(C2H3O2)2]22H2O=478.02
15956-28-2 186-01153 1g 42,000
57-2
186-01011 5g 19,000Rhodium-Activated Carbon (Rh 5%)
- - 184-01012 25g 76,000
2- 57-2
183-01021 5g 18,500Rhodium-Alumina
- 7440-16-6 181-01022 25g 77,000
57-2
Rhodium() Chloride Trihydrate RhCl33H2O =263.31 20765-98-4 - 183-00161 1g 35,500 57-2
Rhodium() Chloride Trihydrate, 99.5%
RhCl33H2O =263.31 20765-98-4 - 181-00841 1g 38,500 57-2
Rhodium() Iodide RhI3=483.62 15492-38-3 - 326-41431 500mg 15,000 57-2Rhodium() Oxide Rh2O3=253.82 12036-35-0 - 183-00421 1g 58,000 57-2
201-12763 250mg 15,000Tetracarbonyldi--chlorodirhodium ()
[Rh2Cl2(CO)4] =388.76 14523-22-9 205-12761 1g 49,500
57-2
RhO
O
P
3
Rh(CO)H
P
2
RhCOCl
Rh
Cl
Rh
Cl
-
36
CAS No. No.
()
Tris(acetylacetonato)rhodium()
(C5H7O2)3Rh =400.23 14284-92-5 - 327-40981
500mg 22,000 57-2
Ru
CAS No. No. ()
Ammonium Hexachlororuthenate() (NH4)2[RuCl6] =349.86 18746-63-9 017-15641 1g 12,300
Bis(2,2'-bipyridine-4,4'-dicarboxylic Acid)bis(thiocyanato)ruthenium() Dihydrate
C26H16N6O8RuS22H2O=741.67 - - 322-53741 50mg 20,000
Carbonylchlorohydridotris(triphenyl- phosphine)ruthenium ()
[RuClH(CO){P(C6H5)3}3]=952.41 16971-33-8 039-15701 1g 11,000
Carbonyldihydridotris(triphenylphos- phine)ruthenium ()
[RuH2(CO){P(C6H5)3}3] =917.97 25360-32-1 030-15471 1g 19,500
Dichloro(1,5-cyclooctadiene)ruthenium(), Polymer
(C8H12Cl2Ru)n 50982-13-3 - 043-26991 1g 26,500
045-22551 1g 5,200Dichlorotris(triphenylphosphine)ruthe- nium()
C54H45Cl2P3Ru =958.85 15529-49-4 041-22553 5g 17,800
Dodecacarbonyltriruthenium (0) [Ru3(CO)12] =639.33 15243-33-1 043-24051 1g 19,500
met-DIRUX
C22H36Cl2Ru2S2 =637.70 216064-20-9 130-14581 200mg 13,000
met-DIRUX-OTf
- 491840-31-4 132-14781 200mg 18,000
Potassium Hexachlororuthenate() K2[RuCl6]=391.98 23013-82-3 161-17691 1g 6,300 182-01851 1g 7,500 Ruthenium() Hydroxyapatite
- - 188-01853 5g 26,000
Ruthenium, Powder, - 45m Ru=101.07 7440-18-8 - 183-01641 1g 14,000 188-01032 25g 10,000Ruthenium-Activated Carbon(Ru 5%)
- - 180-01031 100g 30,000
2-
185-01042 25g 8,200 Ruthenium-Alumina
Ru=101.07 7440-18-8 187-01041 100g 25,000
557-86581 1g 14,400 Ruthenium() Chloride, Anhydrous
RuCl3=207.43 10049-08-8 - SRM44-5850 5g 63,000 187-00821 1g 5,500 Ruthenium() Chloride n-Hydrate,
99.9% RuCl3nH2O 14898-67-0 - 183-00823 10g 35,000
185-01081 1g 7,000 Ruthenium () Oxide, Anhydrous
RuO2=133.07 12036-10-1 Pr. G. 181-01083 5g 27,000 184-00331 100mg 4,400 Ruthenium Red
[(NH3)5RuORu(NH3)4ORu(NH3)5]Cl64H2O=858.42
11103-72-3 180-00333 1g 22,500
323-41561 5g 6,000Trinitratonitrosylruthenium() Nitric Acid Solution (abt 50%)
Ru(NO)(NO3)3 =317.09 34513-98-9 - 321-41562 25g 19,000
- 57-2
Tris(acetylacetonato)ruthenium()
Ru(C5H7O2)3 =398.39 14284-93-6 - 200-15251 1g 9,900
Palladium Catalysts
CAS No. No. ()
Bis(acetonitrile)dichloropalladium () Pd(MeCN)2Cl2 14592-56-4 024-12151 1g 9,000
Bis(dibenzylideneacetone)palladium(0) Pd(dba)2 32005-36-0 329-42021 1g 8,000
320-94201 1g 9,500 [1,2-Bis(diphenylphosphino)ethane]dichloropalladium() PdCl2 (dppe) 19978-61-1
326-94203 5g 35,000
O
O
Rh
3
P
3
RuCl(CO)H
P
3
Ru(CO)H2
Ru
Cl
Cln
O
O
Ru
3
-
37
CAS No. No. ()
327-94211 1g 10,000 [1,1-Bis(diphenylphosphino)ferrocene]dichloropalladium() PdCl2 (dppf) 72287-26-4
323-94213 5g 35,000
324-98741 1g 7,000 [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(), Dichloromethane Adduct
PdCl2(dppf) 95464-05-4320-98743 5g 24,000
354-11081 100mg 7,000 Bis(tri-t-butylphosphine)palladium(0) Pd(t-Bu3P) 2 53199-31-8
350-11083 500mg 18,000
Di- -chlorobis[( -allyl)palladium ()] [PdCl(CH2CHCH2)]2 12012-95-2 048-24241 1g 13,600
327-94191 1g 9,500 trans-Dichlorobis(tricyclohexylphosphine)palladium() trans-PdCl2 (PCy3) 2 29934-17-6
323-94193 5g 35,000
040-22481 1g 4,700 trans-Dichlorobis(triphenylphosphine)palladium() trans-PdCl2(PPh3)2 13965-03-2
046-22483 5g 15,000
163-07141 1g 5,600
169-07143 5g 21,000 Palladium() Acetate Pd(OAc)2 3375-31-3
161-07142 25g 93,000
166-00051 1g 4,500
162-00053 5g 15,000 Palladium() Chloride PdCl2 7647-10-1
164-00052 25g 59,000
209-14643 1g 5,000 Tetrakis(triphenylphosphine)palladium(0) Pd(PPh3)4 14221-01-3
203-14641 5g 16,000
Tris(dibenzylideneacetone)dipalladium(0) Pd(dba)3 52409-22-0 205-14721 1g 16,500
CAS No. / No. ()
557-80001 250mg 9,000
553-80003 1g 15,000 Chloro(di-2-norbornylphosphino)(2'-dimethylamino- 1,1'-biphenyl-2-yl)palladium()
SK-CC01-A [Solvias AG]
551-80004 5g 65,000
554-80011 250mg 9,000
550-80013 1g 15,000 Chloro(di-2-norbornylphosphino)(2-dimethylamino- methylferrocen-1-yl)palladium()
SK-CC02-A [Solvias AG]
558-80014 5g 65,000
556-79961 250mg 9,000
552-79963 1g 15,000 [(IPr)Pd(NQ)]2 Naphthoquinone-1,3-bis(diisopropylphenyl)- imidazole-2-ylidenepalladium(0)
Umicore CX11[Umicore]
550-79964 5g 65,000
553-79971 250mg 9,000
559-79973 1g 15,000 [(IMes)Pd(NQ)]2 Naphthoquinone-1,3-bis(mesityl)imidazole-2- ylidenepalladium(0)
Umicore CX12[Umicore]
557-79974 5g 65,000
550-79981 250mg 9,000
556-79983 1g 15,000 [(IMes)Pd(allyl)]Cl Allylchloro[1,3-bis(mesityl)imidazole-2-ylidene]- palladium()
Umicore CX22[Umicore]
554-79984 5g 65,000
557-79991 250mg 9,000
553-79993 1g 15,000 [(IPr)Pd(allyl)]Cl Allylchloro[1,3-bis(diisopropylphenyl)imidazole-2- ylidene]palladium()
Umicore CX21[Umicore]
551-79994 5g 65,000
321-94231 100mg 12,000 Allylchloro[1,3-bis(2,6-diisopropylphenyl)-2- imidazolidinylidene]palladium()
478980-01-7 Umicore CX23[Umicore] 327-94233 500mg 40,000
325-94251 100mg 12,000 Dichloro[1,3-bis(2,6-diisopropylphenyl)imidazole- 2-ylidene]palladium() Dimer
444910-17-2 Umicore CX41[Umicore] 321-94253 500mg 42,000
328-94241 100mg 12,000 Phenylallylchloro[1,3-bis(diisopropylphenyl)-2- imidazolidinylidene]palladium()
884879-24-7 Umicore CX32[Umicore] 324-94243 500mg 40,000
324-94221 100mg 12,000 Phenylallylchloro[1,3-bis(diisopropylphenyl)-2- imidazol-2-ylidene]palladium()
884879-23-6 Umicore CX31[Umicore] 320-94223 500mg 40,000
Pd
NCl
P
H
PdNMe2
ClP
HFe
N
NPd
O
O
Pd
O
O
N
N
N
NPd
O
O
Pd
O
O
N
N
N
NPd
Cl
N
NPd
Cl
-
38
Pd Ligand No. ()
Di--chlorobis[(-allyl)palladium ()], Supported PEG-PS Resin 043-27731 500mg 20,000
324-56621 1g 7,000 FibreCat1001 [Palladium() Acetate-Triphenylphosphine PE fibres]
2.74 320-56623 5g 24,000
321-56631 1g 8,000 FibreCat1007 [Palladium() Acetate-Dicyclohexylphenylphosphine PE fibres]
34 327-56633 5g 29,000
328-56641 1g 7,000 FibreCat1026 [Acetonitrile Dichloropalladium()-Triphenylphosphine PE fibres]
3.54.5 324-56643 5g 24,000
Palladium()- Hydrotalcite(m) 0.8 168-20553 10g 20,000
Palladium()- Hydrotalcite 1.5 161-20543 5g 20,000
161-21481 1g 10,000
167-21483 5g 35,000 Pd EnCatTM30 3.74.5
169-21482 25g
165-21521 1g 10,000
161-21523 5g 35,000 Pd EnCatTM40 3.94.8
163-21522 25g
168-21491 1g 11,000
164-21493 5g 38,500 Pd EnCatTMTPP30 3.54.5
166-21492 25g
161-21501 1g 11,000
167-21503 5g 38,500 Pd EnCatTMTOTP30 4.25.1
169-21502 25g
161-21981 1g 12,000
167-21983 5g 40,000 Pd()EnCatTMBINAP30 3.75.0
169-21982 25g
168-21991 1g 8,000 PI Palladium abt.3
164-21993 5g 27,000
FibreCat Johnson Matthey Pd EnCatTM Reaxa
C-C/C-N 6 Josiphos 2 Pd-AcetatePd(dba)3
CD-ROM
250mg Solvias SK-CC01-A SK-CC02-A Umicore Umicore CX11 [(IPr)Pd(NQ)]2 Umicore CX12 [(IMes)Pd(NQ)] 2 Umicore CX22 (IMes)Pd(allyl)Cl Umicore CX21 (IPr)Pd(allyl)Cl Josiphos 250mg Solvias SL-J-002-1 SL-J-009-1 Umicore Palladium()-acetate 500 mg Tris(dibenzylideneacetone)-dipalladium(0) 500 mg CD-ROM
No. ()
C-C/C-N Coupling Catalyst Kit Umicore-Solvias 559-79951 1Kit 92,000
-
39
7
Ag
pH
10mM 5-30nm() 6.09.0 PEI
TEM (100k)
Au
pH
10mM 1-4nm() 6.09.0 PEI
TEM (500k)
Ir
pH
10mM 1-4nm() 1.03.0 /IPA PVP
TEM (500k)
Pd
pH
10mM 2-7nm() 2.03.0 /EtOH PVP
TEM (500k)
0
2
4
6
8
10
12
0 2 4 6 8 10 12 14 16 18 20 22 24 26 28 30
nm
Au
02468
10121416
0 2 4 6 8 10 12 14 16 18 20
nm
0
2
4
6
8
10
12
14
0 2 4 6 8 10 12 14 16 18 20
nm
0
1
2
3
4
5
6
7
0 2 4 6 8 10 12 14 16 18 20
nm
-
40
Pt
pH
10mM 1-6nm() 1.02.0 /EtOH PVP
TEM (500k)
Rh
pH
20mM 2-6nm() 1.02.0 /EtOH PVP
TEM (500k)
Ru
pH
20mM 2-6nm() 1.02.0 PVP
TEM (500k)
No. ()
Ag Nanoparticle Dispersion 630-13791 100ml 13,000
Au Nanoparticle Dispersion 633-13781 100ml 15,600
Ir Nanoparticle Dispersion 634-13831 100ml 37,700
Pd Nanoparticle Dispersion 637-13821 100ml 26,000
Pt Nanoparticle Dispersion 636-13771 100ml 18,200
Rh Nanoparticle Dispersion 630-13811 100ml 52,000
Ru Nanoparticle Dispersion 633-13801 100ml 20,800
0
1
2
3
4
5
6
7
0 2 4 6 8 10 12 14 16 18 20
nm)
0
2
4
6
8
10
12
0 2 4 6 8 10 12 14 16 18 20
nm
0
2
4
6
8
10
0 2 4 6 8 10 12 14 16 18 20
nm
-
41
STREM
-
NR4
NR4
Brij35
No. ()
- 250mg 102,000 Gold/tetra-n-octylammonium chloride colloid 2.61.1 nm
79-0080
- 1g 306,000
- 1g 92,400 Platinum-ruthenium/tetra-n-octylammonium chloride colloid (7 wt% Pt, 3.5 wt% Ru)
(7 wt% Pt,3.5 wt% Ru) 2.61.1 nm
78-0062 - 5g 277,200
510-36941 1g 34,900 Platinum colloid (polyethyleneglycol-dodecylether hydrosol)
(10 wt% Pt) 1.20.3 nm
78-0011 - 5g 153,600
513-36931 1g 44,300 Rhodium colloid (polyethyleneglycol-dodecylether hydrosol)
(9 wt% Rh) 2 nm
45-1550 - 5g 202,500
517-36951 1g 27,200 Platinum-ruthenium colloid (polyethyleneglycol-dodecylether hydrosol)
1.3 nm ()
78-0060 - 5g 118,800
Fe/Co
No. ()
512-36901 1ml 20,200
- 5ml 86,400 Cobalt magnetic fluid
8.2 vol% AOT [] LP4 []
27-0001
- 25ml 345,600
519-36891 1ml 15,700
- 5ml 66,000 Iron-cobalt magnetic fluid 0.19 vol% (CNSL)
26-0017
- 25ml 264,000
Fe, Fe/Co Co 1 10nm
102.5nm 60
No. ()
- 1g 22,200 Cobalt nanoparticles, toluene wet 10-12 nm; 27-0026
- 5g 88,500
519-36911 1g 24,400 Cobalt nanoparticles coated with AOT [sodium dioctylsulfosuccinate]
AOT[]
27-0023 - 5g 105,600
512-36881 250mg 25,100 Iron-cobalt nanoparticles, toluene wet 5-8 nm; 26-0011
- 1g 81,900
STREM
MXv + vNR4(BEt3H) M colloid + vNR4X + vB Et3 +(v/2)H2
M XClBr v123 RC6-C20
-
42
Me-BIPAM
Rh Rh Pd
No. ()
(R )-(-)-Me-BIPAM 139-15411 200mg 28,000
(S )-(+)-Me-BIPAM 136-15421 200mg 28,000
1Organic Square, 20, 2 (2007).
O PO
N OP
O
N
O
OAcPd2dba3.CHCl3/ Me-BIPAM
THF, 25 oC, 16 h
H2N NHBn
yield 92%, 92%ee (R, S )
O
+B(OH)2
[Rh(nbd)2]BF4 (3 mol%)BIPAM (3.3 mol%)
NEt3
base, dioxane/H2O
O
yield 99% (R), 99.6%ee
(R) - Me-BIPAM C46H38N2O5P2=760.75
2,2'-[Oxybis(methylene)]bis[dinaphtho[2,1-d :1',2'-f ][1,3,2] dioxaphosphepin-4-yl]dimethylamine] Bisphosphoramidite
CO2Me
NHAc
[Rh(cod)2]PF6 (1 mol%)(R)-Me-BIPAM (1.1 mol%)
H2 (0.3 MPa)THF, 25 oC, 20 h
CO2Me
NHAc
conv.100%(S), 99%eeconv.100%(S),99%ee
-
43
Linked-BINOL
Linked-BINOL 2 BINOL
BINOL
N-
1,2,3 4,5 6
No. ()
3,3-[Oxybis(methylene)]bis-(1R,1R )-1,1-bi-2-naphthol [(R,R )-linked-BINOL] 155-02421 200mg 25,000
3,3-[Oxybis(methylene)]bis-(1S ,1S )-1,1-bi-2-naphthol [(S,S )-linked-BINOL] 152-02431 200mg 25,000
1N. Yoshikawa, N. Kumagai, S. Matsunaga, G. Moll, T. Ohshima, T. Suzuki, M. Shibasaki : J. Am. Chem. Soc., 123, 2466 (2001).
2N. Kumagai, S. Matsunaga, N. Yoshikawa, T. Ohshima, M. Shibasaki : Org. Lett., 3, 1539 (2001).
3M. Shibasaki, M. Kanai, K. Funabashi : Chem. Commun., 1989 (2002).
4Y. S. Kim, S. Matsunaga, J. Das, A. Sekine, T. Ohshima, M. Shibasaki : J. Am. Chem. Soc., 122, 6506 (2000).
5S. Matsunaga, T. Ohshima, M. Shibasaki : Tetrahedron Lett., 41, 8473 (2000).
6S. Harada, S. Matsunaga, M. Shibasaki : Angew. Chem. Int. Ed., 44, 4365 (2005).
-
44
ip-FOXAP
FOXAPFerrocenyl Oxazoli
nyl-Phosphine1
234
50
0 6
No. ()
065-04331 100mg 11,000 ip-FOXAP
061-04333 500mg 44,000
1Y. Nishibayashi, S. Uemura : Synlett, 1, 791995.
2Y. Nishibayashi, I. Takei, S. Uemura, M. Hidai : Organometallics, 17, 34201998.
3I. Takei, Y. Nishibayashi, Y. Arikawa, S. Uemura, M. Hidai : Organometallics, 18, 22711999.
4I. Takei, Y. Nishibayashi, Y. Ishii, Y. Mizobe, S. Uemura, M. Hidai : Chem. Commun., 23602001.
5Y. Nishibayashi, I. Takei, S. Uemura, M. Hidai : Organometallics, 18, 22911999.
6K.-G. Chung, Y. Miyake, S. Uemura : J. Chem. Soc., Perkin Trans.1, 27252000.
(S,S)-[2-(4'-isopropyloxazolin-2'-yl)ferrocenyl]diphenylphosphine ip-FOXAP (Ferrocenyl Oxazolinyl Phosphine)
-
45
Anthracene-9,10-bis5-resorcinol Anthracene-9,10-bis(5-resorcinol)(1)(2)2
Diels-Alder
Zr(Ot-Bu)4
1
Zr(Ot-Bu)4 Diels-Alder 1
No. ()
018-18851 100mg 7,000 Anthracene-9,10-bis(5-resorcinol)
014-18853 1g 35,000
1K.Kobayashi, K. Endo, Y.Aoyama, H.Masuda: Tetrahedoron Lett., 34, 7929 1993.
2aY.Aoyama, Y. Imai, K. Kondo, K. Kobayashi: Tetrahedoron, 51, 3431995.
bK.Kondo, T.Sawaki, M.Koyanagi, K.Kobayashi, H.Masuda, Y. Aoyama: J. Am. Chem. Soc., 117, 83411995.
3K.Kondo, T.Koike, T.Sawaki, O.Hayashida, H. Masuda, Y. Aoyama: J. Am. Chem. Soc., 119, 41171997.
4aT. Sawaki, Y. Aoyama: J. Am. Chem. Soc., 121,47931999.
bT. Sawaki, T. Dewa, Y. Aoyama: J. Am. Chem. Soc., 120, 85391998.
cT. Dewa, Y. Aoyama: J. Mol. Catal. A: Chem., 152, 2572000.
1 2
-
46
Solvias AG
JOSIPHOS Family
CASNo. No.
()
551-80021 100mg 12,000(R)-1-[(S)-2-(Diphenylphosphino)- ferrocenyl]ethyldicyclohexylphosphine (R)-(S)-PPF-Pcy2
[] D20-360 Chem. Purity97%%EE99%
155806-35-2 SL-J001-1
557-80023 250mg 19,000
555-80041 100mg 12,000
551-80043 250mg 18,000
(R)-1-[(S)-2-(Diphenylphosphino)- ferrocenyl]ethyldi-tert-butylphosphine (R)-(S)-PPF-P
tBu2 [] D20-412 Chem. Purity97%%EE99%
155830-69-6 SL-J002-1
559-80044 1g 58,000
552-80051 100mg 12,000(R)-1-[(S)-2-(Dicyclohexylphosphino)- ferrocenyl]ethyldicyclohexylphosphine (R)-(S)-cy2PF-Pcy2
[] D20-139 Chem. Purity97%%EE99%
167416-28-6 SL-J003-1
558-80053 250mg 19,000
559-80061 100mg 12,000(R)-1-[(S)-2-(Diphenylphosphino)- ferrocenyl]ethyldi-3,5-xylylphosphine (R)-(S)-PPF-Pxyl2
[] D20-310 Chem. Purity97%%EE99%
184095-69-0 SL-J005-1
555-80063 250mg 19,000
556-80071 100mg 12,000(R)-1-[(S)-2-(Di-(3,5-bis-trifluoro- methylphenyl)phosphino)ferrocenyl]- ethyldicyclohexylphosphine
(R)-(S)-(3,5-CF3Ph)2PF-Pcy2
[] D20-260 Chem. Purity97%%EE99%
292638-88-1 SL-J006-1
552-80073 250mg 19,000
553-80081 100mg 12,000(R)-1-[(S)-2-(Di-(4-methoxy-3,5-di- methylphenyl)phosphino)ferrocenyl]- ethyldicyclohexylphosphine
(R)-(S)-(4-MeO- 3,5-MePh)2PF- Pcy2
[] D20-270 Chem. Purity97%%EE99%
360048-63-1 SL-J007-1
559-80083 250mg 19,000
550-80091 100mg 12,000(R)-1-[(S)-2-(Di-(3,5-bis-trifluoro- methylphenyl)phosphino)ferrocenyl]- ethyldi(3,5-dimethylphenyl)phosphine
(R)-(S)-(3,5-CF3Ph)2PF-Pxyl2
[] D20-280 Chem. Purity97%%EE99%
166172-63-0 SL-J008-1
556-80093 250mg 19,000
553-80101 100mg 12,000
559-80103 250mg 18,000
(R)-1-[(S)-2-(Dicyclohexylphosphino)- ferrocenyl]ethyldi-tert-butylphosphine
(R)-(S)-cy2PF-P tBu2
[] D20-185 Chem. Purity97%%EE99%
158923-11-6 SL-J009-1
557-80104 1g 58,000
550-80111 100mg 12,000(R)-1-[(S)-2-(Di-(4-trifluoromethyl- phenyl)phosphino)ferrocenyl]ethyldi- tert-butylphosphine
(R)-(S)-(4-CF3 Ph)2-PtBu2
[] D20-352 Chem. Purity97%%EE99%
246231-79-8 SL-J011-1
556-80113 250mg 19,000
558-80031 100mg 12,000(S)-1-[(R)-2-(Di-2-furylphosphino)- ferrocenyl]ethyldi-3,5-xylylphosphine
(S)-(R)-2-Fur2PF- Pxyl2
[] D20+376 Chem. Purity97%%EE99%
649559-66-0 SL-J015-2
554-80033 250mg 19,000
557-81101 100mg 12,000(R)-1-[(S)-2-(Di-1-naphtylphosphino)- ferrocenyl]ethyldi-tert-butylphosphine
(R)-(S)-(1-Naph tyl) 2PF-PtBu2
[] D20-229 Chem. Purity97%%EE99%
849924-43-2 SL-J216-1
553-81103 250mg 19,000
-
47
WALPHOS Family
CASNo. No.
() 557-80121 100mg 12,000
553-80123 250mg 18,000
(R)-1-[(R)-2-(2-Diphenylphosphino- phenyl)ferrocenyl]ethyldi(bis-3,5- trifluoromethylphenyl)phosphine
(R)-(R)-PPPhFCHCH3P((3,5-C F3)2Ph) 2
[] D20-2 Chem. Purity97%%EE99%
387868-06-6 SL-W001-1
551-80124 1g 58,000
554-80131 100mg 12,000(R)-1-[(R)-2-(2-Diphenylphosphino- phenyl)ferrocenyl]ethyldiphenyl- phosphine
(R)-(R)-PPPhFCHCH3PP
[] D20+14 Chem. Purity97%%EE99%
388079-58-1 SL-W002-1
550-80133 250mg 19,000
551-80141 100mg 12,000(R)-1-[(R)-2-(2-Diphenylphosphino- phenyl)ferrocenyl]ethyldicyclohexyl- phosphine
(R)-(R)-PPPhFCHCH3Pcy2
[] D20-8 Chem. Purity97%%EE99%
388079-60-5 SL-W003-1
557-80143 250mg 19,000
558-80151 100mg 12,000(R)-1-[(R)-2-{2-Di(3,5-dimethyl-4- methoxyphenyl)phosphinophenyl}- ferrocenyl]ethyldi(bis-3,5-trifluoro- methylphenyl)phosphine
(R)-(R)-(3,5-Me-4-MeO-Ph)2-PPhFCHCH3P(3,5-CF3Ph)2
[] D20+19 Chem. Purity97%%EE99%
494227-30-4 SL-W005-1
554-80153 250mg 19,000
555-80161 100mg 12,000(R)-1-[(R)-2-(2-Diphenylphosphino- phenyl)ferrocenyl]ethyldi-(3,5-xylyl)- phosphine
(R)-(R)-PPPhFCHCH3Pxyl2
[] D20+21 Chem. Purity97%%EE99%
494227-31-5 SL-W006-1
551-80163 250mg 19,000
552-80171 100mg 12,000(R)-1-[(R)-2-(2-Dicyclohexylphos- phinophenyl)ferrocenyl]ethyldi(bis-3,5-trifluoromethylphenyl)phosphine
(R)-(R)-cy2PPhFCHCH3P(3,5-CF3Ph)2
[] D20+10 Chem. Purity97%%EE99%
494227-32-6 SL-W008-1
558-80173 250mg 19,000
559-80181 100mg 12,000(R)-1-[(R)-2-(2-Di-(3,5-xylyl)phos- phinophenyl)ferrocenyl]ethyldi(3,5- xylyl)phosphine
(R)-(R)-xyl2PPhFCHCH3Pxyl2
[] D20+7 Chem. Purity97%%EE99%
494227-33-7 SL-W009-1
555-80183 250mg 19,000
TANIAPHOS Family
CASNo. No.
()
558-80271 100mg 12,000(S)-1-Diphenylphosphino-2-[(R)-- (N,N-dimethylamino)-o-diphenyl- phosphinophenylmethyl]ferrocene
(R)-(S)-PPPhCHNMe2-F-PP
[] D20+312 Chem. Purity97%%EE99%
255884-98-1 SL-T001-1
554-80273 250mg 19,000
555-80281 100mg 12,000(S)-1-Dicyclohexylphosphino-2-[(R)- -(N,N-dimethylamino)-o-dicyclohexyl- phosphinophenylmethyl]ferrocene
(R)-(S)-cy2PPhCHNMe2-F-Pcy2
[] D20+110 Chem. Purity97%%EE99%
494227-38-2 SL-T002-1
551-80283 250mg 19,000
-
48
MANDYPHOS Family
CASNo. No.
()
556-80191 100mg 12,000(R,R)-2,2-Bis(-N,N-dimethyl- aminophenylmethyl)-(S,S)-1,1-bis- (diphenylphosphino)ferrocene
(R)-(S)-NMe2-P Ph2-Mandyphos
[] D20-320 Chem. Purity97%%EE99%
210842-74-3 SL-M001-1
552-80193 250mg 19,000
559-80201 100mg 12,000(R,R)-2,2-Bis(-N,N-dimethyl- aminophenylmethyl)-(S,S)-1,1-bis- (dicyclohexylphosphino)ferrocene
(R)-(S)-NMe2- Pcy2-Mandyphos
[] D20+54 Chem. Purity97%%EE99%
494227-35-9 SL-M002-1
555-80203 250mg 19,000
554-81111 100mg 12,000(R,R)-2,2-Bis(-N,N-dimethyl- aminophenylmethyl)-(S,S)-1,1-bis- [di(bis(3,5-trifluoromethyl)phenyl)- phosphino]ferrocene
(R)-(S)-NMe2-P (3,5-CF3Ph)2- Mandyphos
[] D20-250 Chem. Purity97%%EE99%
494227-36-0 SL-M003-1
550-81113 250mg 19,000
556-80211 100mg 12,000
552-80213 250mg 18,000
(R,R)-2,2-Bis(-N,N-dimethyl- aminophenylmethyl)-(S,S)-1,1-bis- [di(3,5-dimethyl-4-methoxyphenyl)- phosphino]ferrocene
(R)-(S)-NMe2-P (3,5-Me-4-MeO Ph)2-Mandyphos
[] D20-61 Chem. Purity97%%EE99%
494227-37-1 SL-M004-1
550-80214 1g 58,000
553-80221 100mg 12,000
559-80223 250mg 18,000
(R,R)-2,2-Bis(-N,N-dimethyl- aminophenylmethyl)-(S,S)-1,1-bis- [di(3,5-dimethylphenyl)phosphino]- ferrocene
(R)-(S)-NMe2-P Xyl2-Mandyphos
[] D20-164 Chem. Purity97%%EE99%
793718-16-8 SL-M009-1
557-80224 1g 58,000
550-80231 100mg 12,000(R,R)-2,2-Bis(-N,N-dimethyl- aminophenylmethyl)-(S,S)-1,1-bis- [di(2-methylphenyl)phosphino]- ferrocene
(R)-(S)-NMe2-Po
Tol2-Mandyphos
[] D20-196 Chem. Purity97%%EE99%
831226-37-0 SL-M012-1
556-80233 250mg 19,000
BUTIPHANE Family
CASNo. No.
() 557-80241 100mg 12,000
553-80243 250mg 18,000
1,2-Bis[(2S,5S)-2,5-dimethyl-(3S,4S)-3,4-dihydroxyphospholano]benzene Bis(trifluoromethanesulfonate)salt
[] D20+146 Chem. Purity97%%EE99%
552829-96-6 SL-P001-2
551-80244 1g 58,000
554-80251 100mg 12,000(R,R)-2,3-Bis(2,5-dimethylphospho- lan-1-yl)benzo[b]thiophene cyclo- octadiene Rh() tetrafluoroborate
[((R,R)-Me- Butiphane)Rh(COD)]BF4
[] D20-54 Chem. Purity97%%EE99%
511543-00-3 SK-P005-1a
550-80253 250mg 19,000
-
49
Maruoka Catalyst
(R,R)-3,4,5-Trifluorophenyl-NAS Bromide
-
1)
(R,R)-3,5-Bistrifluoromethylphenyl-NAS
Bromide
---
2)
- 1 --- 2
No. ()
201-15921 100mg 30,000 (R,R)-3,4,5-Trifluorophenyl-NAS Bromide
207-15923 500mg
201-16401 100mg 30,000 (S,S)-3,4,5-Trifluorophenyl-NAS Bromide
207-16403 500mg
029-14921 100mg 30,000 (R,R)-3,5-Bistrifluoromethylphenyl-NAS Bromide
025-14923 500mg
026-16251 100mg 30,000 (S,S)-3,5-Bistrifluoromethylphenyl-NAS Bromide
022-16253 500mg
1T. Ooi, M. Kameda, H. Tannai, K. Maruoka : Tetrahedron Lett., 41, 83392000.
2T. Ooi, M. Taniguchi, M. Kameda, K. Maruoka : Angew. Chem. Int. Ed., 41, 45422002).
-
50
2-Azaadamantane-N-oxylAZADO 1-Methyl-2-azaadamantane-N-oxyl1-Me-AZADO
1) IBX Dess-Martin TEMPO[2,2,6,6-tetramethyl 1-
pineridinyloxy] 2 TEMPO
0.01molTEMPO 20 2 OH
Anelli TEMPO 1-Me-AZADO
loading yield (%)
amount (mol%) TEMPO 1-Me-AZADO
0.1 96 95
0.01 23 91
0.004 n.d. 88a
0.001 n.d. 62b a The run time was 30 min. b The run time was 60 min.
Margarita TEMPO 1-Me-AZADO
loading yield (%) / time (h)
amount (mol%) TEMPO 1-Me-AZADO
10 95/1.5 96/0.1
1 42/6 93/0.7
0.1 n.d. 39/3
NO .
NO .
N
O .2-Azaadamantane-N-oxyl
AZADO 2,2,6,6-tetramethyl 1-pineridinyloxy
TEMPO1-Methyl-2-azaadamantane-N-oxyl
1-Me-AZADO
-
51
2 TEMPO 1-Me-AZADO
yielda (%) yielda (%) entry substrate method
TEMPO 1-Me-AZADO entry substrate method
TEMPO 1-Me-AZADO
1
A 83 94
7
A 15 93
57 87 2
A 84 99
8
A
3
A 68 97
A 8 99
9
Ab 90 4
A 0 94
A n.d.c 19
5
A 16 99
10
B 12c 100
6
A 5 95 A n.d.c 10
11
B 27e 46e Method A: reactions were catalyzed by TEMPO or 1-Me-AZADO (1 mol%) with NaOCl (150 mol%), KBr (10 mol%), Bu4NBr (5 mol%), aq. NaHCO3 in CH2Cl2 at 0 for 20min. Method B: reactions were catalyzed by TEMPO or 1-Me-AZADO (1 mol%) with 1.1. equiv. of PhI (OAc)2 in CH2Cl2 for 9 h at rt. a: Isolated yield. b: reaction was run using 20 g of substrate. c: Not determined. d: Reaction was run using 3.3 equiv. of PhI (OAc)2 for 14 h at rt. e: Reaction was run using 5.1 equiv. of PhI (OAc)2 for 30 h at rt.
No. ()
014-22001 100mg 8,000
010-22003 500mg 24,000 2-Azaadamantane-N-oxyl AZADO
018-22004 1g 36,000
132-15261 100mg 8,500 1-Methyl-2-azaadamantane-N-oxyl 1-Me-AZADO
138-15263 500mg 29,000
1M.Shibuya, M.Tomizawa, I.Suzuki, Y.Iwabuchi J. Am. Chem. Soc.128, 84122006.
Kawabata Acylation Catalyst 4
4
No. ()
Kawabata Acylation Catalyst 119-00781 50mg 18,000
1T.Kawabata, W.Muramatsu, T.Nishio, T.Shibata, H.Schedel :J.Am.Chem.Soc., 129, 12890 (2007).
2, 76 (4), 16 (2008).
2,5-[4-(N-Pyrrolidinyl)pyridine]bis[(2-acetylamido)- 3-(1H-indol-3-yl)]propionic Acid Octyl Ester C49H60N6O6 = 829.04
N
N
OO
HN HN
O
OO
O
NHHN
>99% selective98% yield
1. TBDMSCl / imidazole2. 2-methoxypropene / PPTS3. (i-PrCO)2O / DMAP
4. CSA / MeOH5. separation of regioisomers 46% overall
OX
OHHO
HOHO
OX
OHHO
HOi-PrCOO
(i-PrCO)2O4 4
(a)catalytic one-step process
(b)conventional protection/ deprotection procedure
Kawabata Acylation Catalyst
-
52
(R)-NP-NAP
Mannich-Type Reaction1
No. ()
(R)-NP-NAP 145-07861 200mg 15,000
1T. Akiyama, J. Itoh, K. Yokota, K. Fuchibe : Angew. Chem. Int. Ed., 43, 1566 (2004).
(R)-(-)-3,3-Bis(4-nitrophenyl)-1,1-binaphthyl-2,2-diyl Hydrogen Phosphate
Ar =4-NO2C6H4
C32H19N2O8P=590.48
-
53
TaDiAS
4
2 4
-
1a,1c
-
1b,1d
12
Tartrate-derived Diammonium Salt
-
No. ()
TaDiAS-[(4S,5S)-2-t-butyl-2-methyl-N,N,N,N- tetrakis(4-methoxybenzyl)]Diiodide1 208-16151 100mg 8,500
TaDiAS-[(4R,5R)-2-t-butyl-2-methyl-N,N,N,N- tetrakis(4-methoxybenzyl)]Diiodide 201-16141 100mg 8,500
TaDiAS-[(4S,5S)-2,2-dipropyl-N,N,N,N- tetrakis(4-methylbenzyI)]Bis(tetrafluoroborate)2 202-16171 100mg 8,500
TaDiAS-[(4R,5R)-2,2-dipropyl-N,N,N,N- tetrakis(4-methylbenzyl)]Bis(tetrafluoroborate) 205-16161 100mg 8,500
11a21d
1T. Shibuguchi, Y. Fukuta, Y. Akachi, A. Sekine, T. Ohshima, M. Shibasaki : Tetrahedron Lett., 43, 95392002.
2T. Ohshima, V. Gnanadesikan, T. Shibuguchi, Y. Fukuta, T. Nemoto, M. Shibasaki : J. Am. Chem. Soc., 125, 112062003.
-
54
DCKEA
1
2
3
1 2 3 Mannich 4
No. ()
Dicyanoketene Ethylene Acetal DCKEA 044-29581 500mg 8,000
1T. Miura, Y. Masaki : Tetrahedron Lett., 35, 7961 1994.
2N. Tanaka, Y. Masaki : Synlett, 1277 1999.
3N. Tanaka, Y. Masaki : Synlett, 1960 1999.
4N. Tanaka, Y. Masaki : Synlett, 406 2000.
5964-65-5
-
55
-
N-Methyl-4-pyridineboronic Acid Iodide 4-1
[emim] [OTf] 2
1
No. ()
130-15181 100mg 6,000 N-Methyl-4-pyridineboronic Acid Iodide
132-15185 500mg 19,000
1S. Ohara, K. Ishihara, H. Yamamoto : The 77th Spring Meeting of Chemical Society of Japan, 3-B5-10 2000.
2T. Maki, K. Ishihara, H. Yamamoto : Organic Lett., 7, 5043 2005.
3T. Maki, K. Ishihara, H. Yamamoto : Organic Lett., 7, 5047 2005.
Polystyrene-bound N-Methyl-4-pyridineboronic Acid Chloride 4-2N-Methylboronopyridinium Chloride
No. ()
165-22241 100mg 6,000 Polystyrene-bound N-Methyl-4-pyridineboronic Acid Chloride
161-22243 500mg 19,000
1S. Ohara, K. Ishihara, H. Yamamoto : The 77 th Spring Meeting of Chemical Society of Japan, 3-B5-10 2000.
2T. Maki, K. Ishihara, H. Yamamoto : Organic Lett., 7, 5043 2005.
3T. Maki, K. Ishihara, H. Yamamoto : Organic Lett., 7, 5047 2005.
1 CAS No.362045-65-6
2
-
56
CAS No. No. ()
126-05231 5g 6,500 Lanthanum Trifluoromethanesulfonate1)2)3) (CF3SO3)3 La =586.11 52093-26-2 124-05232 25g 20,000
147-08301 5g 5,500 Neodymium Trifluoromethanesulfonate (CF3SO3)3Nd =591.45 34622-08-7 145-08302 25g 21,000
531-78691 1g 12,500 Scandium()Trifluoromethanesulfonate4)5) (CF3SO3)3 Sc =492.16 144026-79-9 - SRM21-2000 5g 51,600
205-16421 5g 10,000 Thulium Trifluoromethanesulfonate (CF3SO3)3 Tm =616.14 141478-68-4 203-16422 25g 39,000
254-00521 5g 5,300 Ytterbium()Trifluoromethanesulfonate n-Hydrate6)7)8)
(CF3SO3)3YbnH2O=620.25 (as anhyd.)
54761-04-5 252-00522 25g 17,500
1S. Kobayashi : Synlett, 6891994.
2J. Inanaga, Y. Yokoyama, T. Hanamoto : Tetrahedron Lett., 34, 27911993.
3J. H. Forsberg, V. T. Spaziano, T. M. Balasubramanian, G. K. Liu, S. A. Kinsley, C. A. Duckworth, J. J. Poteruca,
P. S. Brown, J. L. Miller : J. Org. Chem., 52, 10171987.
4S. Kobayashi, I. Hachiya, M. Araki, H. Ishitani : Tetrahedron Lett., 34, 37551993.
5S. Kobayashi : Synlett, 6891994.
6S. Kobayashi, I. Hachiya, T. Takahori : Synthesis, 3711993.
7S. Kobayashi, I. Hachiya : J. Org. Chem., 59, 35901994.
8S. Kobayashi : Synlett, 6891994.
CAS No. No. ()
038-19671 5g 6,000 Copper()Trifluoromethanesulfonate1) (CF3SO3)2Cu
=361.68 34946-82-2
036-19672 25g 18,000
099-05351 5g 7,500 Iron()Trifluoromethanesulfonate (CF3SO3)2Fe
=353.98 59163-91-6
097-05352 25g 24,000
Lithium Trifluoromethanesulfonate CF3SO3Li=156.01 33454-82-9 97 128-03792 25g 6,300
Potassium Trifluoromethanesulfonate CF3SO3K=188.17 2926-27-4 97 167-15312 25g 7,300
Sodium Trifluoromethanesulfonate CF3SO3Na=172.06 2926-30-9 95 193-10052 25g 7,300
195-10931 10g 8,000 Silver Trifluoromethanesulfonate2)3) CF3SO3Ag=256.94 2923-28-6 97
191-10933 50g 32,000
266-01861 10g 6,000 Zinc Trifluoromethanesulfonate (CF3SO3)2Zn
=363.55 54010-75-2
262-01863 50g 20,000
1Y. Nakamura, R. Matsubara, H. Kiyohara, S. Kobayashi : Org. Lett., 5, 24812003.
2S. Koto, T. Sato, N. Morishima, S. Zen : Bull. Chem. Soc. Jpn., 53, 17611980.
3V. Pozsgay, T. Ohgi, S. M. Hecht : J. Org. Chem., 46, 37611981.
-
57
No. ()
(R)-2,2-Binaphthyl-14-crown-4
023-14681 1g 22,000
(S)-2,2-Binaphthyl-14-crown-4
020-14691 1g 22,000
(R)-2,2-Binaphthyl-17-crown-5
023-14701 1g 22,000
(S)-2,2-Binaphthyl-17-crown-5
020-14711 1g 22,000
(S)-2,2-Binaphthyl-20-crown-6
024-14731 1g 24,000
1S. Nagayama, S. Kobayashi : J. Am. Chem. Soc., 122, 115312000.
CAS No. No. ()322-27851 100mg 3,500
4'-Aminobenzo-15-crown-5 C14H21NO5=283.32 60835-71-4 - 328-27853 500mg 9,000 1-Aza-18-crown-6 C12H25NO5=263.33 33941-15-0 - 328-74461 1g 15,000
326-45191 1g 7,000 Benzo-12-crown-4 C12H16O4=224.25 14174-08-4 - 322-45193 5g 23,000
324-31461 1g 6,500 Benzo-18-crown-6 C16H24O6=312.36 14098-24-9 - 320-31463 5g 20,000
032-17393 1ml 7,500 12-Crown-4 C8H16O4=176.21 294-93-9 - 036-17391 5ml 17,000 15-Crown-5 C10H20O5=220.26 33100-27-5 035-16901 10ml 12,000
033-12541 5g 2,500 031-12542 25g 8,000 18-Crown-6 C12H24O6=264.32 17455-13-9 039-12543 100g 24,000
1,7-Diaza-12-crown-4 C8H18N2O2=174.24 294-92-8 - 325-74471 250mg 18,000 321-31471 1g 6,000
Dibenzo-15-crown-5 C18H20O5=316.35 14262-60-3 - 327-31473 10g 33,000 042-26221 5g 4,500
Dibenzo-18-crown-6 C20H24O6=360.40 14187-32-7 - 040-26222 25g 14,000 329-45181 1g 7,000
Dibenzo-24-crown-8 C24H32O8=448.51 14174-09-5 - 325-45183 5g 23,000 328-23671 100mg 5,000
Dibenzo-30-crown-10 C28H40O10=536.61 17455-25-3 - 324-23673 1g 21,000 322-45171 1g 8,000
4,4'-Dibromodibenzo-18-crown-6 C20H22Br2O6 =518.19 87016-67-9 - 328-45173 5g 27,000 327-31451 1g 3,800
cis-Dicyclohexano-18-crown-6 C20H36O6=372.50 16069-36-6 - 323-31453 5g 19,000 Dicyclohexano-24-crown-8 C24H44O8=460.60 17455-23-1 - 042-26721 1g 13,500
320-31441 1g 7,500 4,4'(5')-Di-t-butyldibenzo-18-crown-6 C28H40O6=472.61 29471-17-8 - 326-31443 5g 27,000 2-(Hydroxymethyl)-15-crown-5 C11H22O6=250.29 75507-25-4 - 322-79361 1g 15,000 2-(Hydroxymethyl)-18-crown-6 C13H26O7=294.34 70069-04-4 - 327-74291 1g 20,000
324-54921 1g 8,000 Icosafluoro-15-crown-5 C10F20O5=580.07 97571-69-2 - 320-54923 5g 27,000
1
-
58
18--6
18--6
1-(2--18--6)-3- (50mg, 0.1mmol, 0.2eq) 1--3-(5ml) (80, 5 )0.5mmol(0.75mmol)
1-(2--18--6)-3- 1--3-( 5ml)(10ml)(1ml) 4 80 5
No. ()
134-14981 100mg 8,000 1-(2-Methyl-18-crown-6)-3-methylimidazolium Hexafluorophosphate
130-14983 500mg 28,000
1-(2-Methyl-18-crown-6)-3-methylimidazolium Hexafluorophosphate C17H31N2O6PF6=504.40
-
59
Ionic Liquid 1
Aldol Diels-Alder
Aldol Diels-Alder
1, 30, No.17,5 2001.
Imidazolium
CAS No. No. ()
013-20491 5g 9,000 1-Allyl-3-methylimidazolium Chloride 65039-10-3
011-20492 25g 35,000
029-15761 5g 5,000 1-Butyl-2,3-dimethylimidazolium Chloride mp 89 98892-75-2
027-15762 25g 16,500
022-15751 5g 8,000 1-Butyl-2,3-dimethylimidazolium Hexafluorophosphate mp 39 227617-70-1 020-15752 25g 28,000
024-16171 5g 9,000 1-Butyl-2,3-dimethylimidazolium Iodide 108203-70-9
022-16172 25g 32,000
329-87181 5g 7,000 1-Butyl-2,3-dimethylimidazolium Tetrafluoroborate 402846-78-0 327-87182 25g 25,000
026-15771 1g 7,000 1-Butyl-3-methylimidazolium Bis(trifluoromethylsulfonyl)imide 174899-83-3 022-15773 5g 24,000
CAS No.145022-44-2
yield:84%
yield:80%endo/exo:1.7/1
NN+
Cl-
NN+
Cl-
NN+
PF6-
NN+
I-
NN+
BF4-
NN+
(CF3SO
2)2N-
-
60
CAS No. No. ()
027-15201 5g 3,800 1-Butyl-3-methylimidazolium Chloride mp 67 79917-90-1
025-15202 25g 9,800
024-15211 5g 6,500 1-Butyl-3-methylimidazolium Hexafluorophosphate 174501-64-5 022-15212 25g 19,000
327-86401 5g 7,000 1-Butyl-3-methylimidazolium Tetrachloroferrate() 359845-21-9 325-86402 25g 21,000
027-15181 5g 6,400 1-Butyl-3-methylimidazolium Tetrafluoroborate 174501-65-6
025-15182 25g 21,000
024-15191 1g 5,500 1-Butyl-3-methylimidazolium Trifluoromethanesulfonate 174899-66-2 020-15193 5g 19,000
326-87191 5g 12,000 1-Ethyl-2,3-dimethylimidazolium Hexafluorophosphate 292140-86-4 324-87192 25g 45,000
050-07401 5g 8,500 1-Ethyl-2,3-dimethylimidazolium Tetrafluoroborate mp 92 307492-75-7 058-07402 25g 30,000
052-07601 1g 8,000 1-Ethyl-3-methylimidazolium Bis(trifluoromethylsulfonyl)imide 174899-82-2 058-07603 5g 28,000
055-07331 5g 4,800 1-Ethyl-3-methylimidazolium Bromide mp 71 65039-08-9
053-07332 25g 16,000
056-07621 5g 8,000 1-Ethyl-3-methylimidazolium Hexafluorophosphate mp 61 155371-19-0 054-07622 25g 28,000
054-07301 5g 9,500 1-Ethyl-3-methylimidazolium Tetrafluoroborate 143314-16-3
052-07302 25g 35,000
051-07311 5g 7,000 1-Ethyl-3-methylimidazolium p-Toluenesulfonate mp 51 328090-25-1
059-07312 25g 25,000
057-07411 5g 11,000 1-Ethyl-3-methylimidazolium Trifluoroacetate 174899-65-1
055-07412 25g 40,000
1-Ethyl-3-methylimidazolium Trifluoromethanesulfonate 145022-44-2 059-07111 10g 20,000
085-08191 5g 7,000 1-Hexyl-3-methylimidazolium Hexafluorophosphate 304680-35-1 083-08192 25g 26,000
088-08821 5g 7,000 1-Hexyl-3-methylimidazolium Iodide 178631-05-5
086-08822 25g 24,000
088-08201 5g 7,500 1-Hexyl-3-methylimidazolium Tetrafluoroborate 244193-50-8
086-08202 25g 28,000
132-15381 5g 6,500 1-Methyl-3-octylimidazolium Chloride 64697-40-1
130-15382 25g 22,500
138-14761 5g 8,000 1-Methyl-3-octylimidazolium Hexafluorophosphate 304680-36-2 136-14762 25g 30,000
135-14771 5g 8,000 1-Methyl-3-octylimidazolium Tetrafluoroborate 244193-52-0
133-14772 25g 25,000
131-15851 5g 7,000 1-Methyl-3-propylimidazolium Iodide 119171-18-5
139-15852 25g 24,000
NN+
Cl-
NN+
PF6-
NN+
FeCl4-
NN+
BF4-
NN+
CF3SO
3-
NN+
PF6-
NN+
BF4-
NN+
(CF3SO2)2N-
NN+
Br-
NN+
PF6-
NN+
BF4-
NN+
SO3-
NN+
CF3CO2-
NN+
CF3SO3-
NN+
PF6-
NN+
I-
NN+
BF4-
NN+
Cl-
NN+
PF6-
NN+
BF4-
NN+
I-
-
61
Pyrrolidinium, Piperidinium
CAS No. No. ()
325-87281 5g 8,500 1-Butyl-1-methylpyrrolidinium Hexafluorophosphate 330671-29-9 323-87282 25g 32,000
027-16161 5g 8,000 1-Butyl-1-methylpyrrolidinium Iodide 56511-17-2
025-16162 25g 28,000
322-87291 5g 8,000 1-Butyl-1-methylpyrrolidinium Tetrafluoroborate mp 150 345984-11-4
320-87292 25g 30,000
027-15441 5g 7,800 1-Butyl-1-methylpyrrolidinium Bis(trifluoromethanesulfonyl)imide