Organometallics

Mechanistic Investigations of Cu-Catalyzed Fluorination of Diaryliodonium Salts: Elaborating the CuI/CuIII Manifold in

CopperCatalysis Naoko Ichiishi, Allan J. Canty, Brian F. Yates, and Melanie S. Sanford,

Organometallics 2014, 33, 55255534

Chemical Communications

Relay cooperation of K2S2O8 and O2 in oxytrifluoromethylation of alkenes using CF3SO2Na

Qingquan Lu, Chao Liu, Zhiyuan Huang, Yiyang Ma, Jian Zhanga and Aiwen Lei

Chem. Commun., 2014, 50, 14101--14104

K2S2O8(25 mol%)

450C, DMSO

X

R1

R2

R1

O

CF3

R2

CF3SO2Na O2(air)

Direct CH difluoromethylenephosphonation of arenes and heteroarenes with bromodifluoromethyl phosphonate via visible-light

photocatalysis Lin Wang, Xiao-Jing Wei, Wen-Long Lei, Han Chen, Li-Zhu Wub and Qiang Liu

Oxidative tandem nitrosation/cyclization of N-arylenamines with nitromethane toward3-(trifluoromethyl)quinoxalines

Zhi-Jun Yang, Chuan-Zhuo Liu, Bo-Lun Hu, Chen-Liang Deng and Xing-Guo Zhang

Chem. Commun., 2014, 50, 1455414557

HN

Ph

CF3

N

N CF3

Ph N

N CF3

Ph

O

CH3NO2

CatalistOxidant

Additive

HN

R'

CF3

N

N CF3

R'

CH3NO2

10 mol% KITBHP (2.5 equiv.)

CsOAc (2.5 equiv.)

HOAc (2 equiv.)

1200C, N2

R R

Chem. Commun., 2014, 50, 15916--15919

CHEMISTRY An Asian Journal

Synthesis of Pyridine N-OxideBF2CF3 Complexes and Their FluorescenceProperties

Tomoaki Nishida, Aiko Fukazawa, Eriko Yamaguchi, Hiroya Oshima, Shigehiro Yamaguchi, Motomu Kanai, and Yoichiro Kuninobu

Chem. Asian J. 2014, 9, 1026 1030

New reagent

BF2CF3 complex with 4-phenylpyridine N-oxide

K[BF3CF3]

BF3OEt2(1.1 equiv.)

CH2Cl2250C, 20 min

[BF2CF3OEt2]

N

Ph

O

N

Ph

OBF2CF3

(1.0 equiv.)

CH2Cl2250C, 1h

89%

(1.1 equiv.)

Stereoselective Nucleophilic Addition of PhSCF2SiMe3 to Chiral Cyclic Nitrones: Asymmetric Synthesis of gem-Difluoromethylenated

Polyhydroxypyrrolizidines and-indolizidines Korkit Korvorapun, Darunee Soorukram, Chutima Kuhakarn, Patoomratana

Tuchinda,Vichai Reutrakul, and Manat Pohmakotr

Chem. Asian J. 2015, 10, 948 968

Organic Letters

Difluorohomologation of Ketones

Mikhail D. Kosobokov, Vitalij V. Levin, Marina I. Struchkova, and Alexander D. Dilman Org. Lett. 2015, 17, 760763

R1

O

R3

R2

R1

O

F F

R3

R2

(a)Mo3SiOTf, NEt3dioxane, rt, 40 min

(b)Mo3SiCF2Br, HMPA, rt, 3 h

(c)HBr/AcOH, H2O, 800C, 1 h

Journal og Organic Chemistry

Nonafluorobutanesulfonyl Azide as a Shelf-Stable Highly Reactive Oxidant for the Copper-Catalyzed Synthesis of 1,3-Diynes from

Terminal Alkynes JoseRamon Suarez, Daniel Collado-Sanz, Diego J. Cardenas, and Jose Luis Chiara

J. Org. Chem. 2015, 80, 10981106

2NfN3(0.6 equiv), DBU(0.6 equiv)

CuI(2 mol%), CHCl3, rt, 10 minR RR

Chloro, Difluoromethylation and Chloro, Carbomethoxydifluoromethylation: Reaction of Radicals Derived from

RfSO2Cl with Unactivated Alkenes under Metal-Free Conditions

Charles S. Thomoson, Xiao-Jun Tang, and William R. Dolbier, Jr.

J. Org. Chem. 2015, 80, 12641268

Cl S

O

O

CF2H R

Cl

RCF2H

DLP(0.4 equv.)

700C, DCM, 8 h

O

MeOS DLP(0.4 equv.)

700C, DCM, 8 h

O

O

Cl

F F

Cl

O

MeO

F F

Synthesis of Vinyl Trifluoromethyl Thioethers via Copper-

MediatedTrifluoromethylthiolation of Vinyl Bromides

Yangjie Huang, Jianping Ding, Chuyi Wu, Huidong Zheng, and Zhiqiang Weng.

J. Org. Chem. 2015, 80, 29122917

R

R1

Br

R2

R

R1

SCF3

R2

(bpy)Cu(SCF3)

KF(4 equiv.)Diglime

1000C, 24 h

http://pubs.acs.org/action/doSearch?ContribStored=Thomoson%2C+C+Shttp://pubs.acs.org/action/doSearch?ContribStored=Tang%2C+Xhttp://pubs.acs.org/action/doSearch?ContribStored=Dolbier%2C+W+R+Jr.

Synthesis of Trifluoromethyl-Containing Vicinal Diamines by Asymmetric Decarboxylative Mannich Addition Reactions

Lingmin Wu, Chen Xie, Haibo Mei, Yanling Dai, Jianlin Han, Vadim A. Soloshonok,and Yi Pan.

J. Org. Chem. 2015, 80, 31873194

CHEMISTRY A European Journal Communication

Stable but Reactive Perfluoroalkylzinc Reagents: Application in Ligand-Free Copper-Catalyzed Perfluoroalkylation of Aryl Iodides

Kohsuke Aikawa, Yuzo Nakamura, Yuki Yokota, Wataru Toya, and Koichi Mikami

Chem. Eur. J. 2015, 21, 96 100

RI

RRF

[A] Zn(C2F5)2(DMPU)2 (1 equiv.)

CuI (10 mol%)

DMPU, 900C, 24 h

[B] Zn(nC6F13)2(DMPU)2 (1 equiv.)

CuI (10 mol%)

DMPU, 1200C, 24 h

Ph

I

Ph

RF

[A] or [B]

Pd-Catalyzed Difluoromethylation of Vinyl Bromides, Triflates, Tosylates, and Nonaflates

Dalu Chang, Yang Gu, and Qilong Shen

Chem. Eur. J. 2015, 21, 6074 6078

RBr

[(SIPr)Ag(CF2H)]

(1.0 equiv.)

1.0 mol% [Pd}2.0 mol% DPPF

dioxane

600C, 24 h

RCF2H

[(SIPr)Ag(CF2H)]

(1.2 equiv.)

1.0 mol% [Pd}2.0 mol% DPPF

KBr (2.0 equiv.)

dioxane

600C, 24 h

R

R'

OTf/ONf

R''

R

R'

CF2H

R''

[(SIPr)Ag(CF2H)]

(1.2 equiv.)

1.0 mol% [Pd}2.0 mol% DPPF

KBr (2.0 equiv.)

dioxane

800C, 24 h

R

R'

OTs

R''

R

R'

CF2H

R''

European Journal og Organic Chemistry

Modified Julia Olefination on Sugar-Derived Lactones: Synthesis of Difluoroexo-glycals

Samuel Habiba] and David Gueyrard

Eur. J. Org. Chem. 2015, 871875

Metal-Mediated Reformatsky Reaction of Bromodifluoromethyl Ketone and Imine

Chun-Ru Cao, Min Jiang, and Jin-Tao Liu

Eur. J. Org. Chem. 2015, 1144 1151

Copper-Catalyzed Innate Ethoxycarbonyldifluoromethylation of Electron-Rich Arenes

Marie-Charlotte Belhomme, Alexandre Bayle, Thomas Poisson, and Xavier Pannecoucke

Eur. J. Org. Chem. 2015, 1719 1726

EDG

R

H

EDG

R

CF2COX

Cu2O (% mol%), L1 (12 mol %)

K2CO3, BrCF2COX

DMF, 800C, 16 h

Journal of Fluorine Chemistry

Nucleophilic tetrafluoroethylation of carbonyl compounds with fluorinated sulfones

Jir Vaclavk , Yana Chernykh, Bronislav Jurasek, Petr Beier

J. Fluor. Chem. 2015, v.169, pp 2431

R1 R2

O

CF2CF2SO2PhR2

OH

R1 PhSO2CF2CF2CF2H

1. PhSO2CF2CF2SiMe3CsF, DMF, -500C to rt

2. HCl, H2O, rt

CF2CF2SO2PhR2

OH

R1

Route A:

Na, EtOH, THF, rt

Route B:

Mg, MeOH, rt

CF2CF2HR2

OH

R1

General asymmetric synthesis of 2,2,2-trifluoro-1-(1H-indol-3- and -2-yl)ethanamines

Lingmin Wu, Chen Xie, Jie Zhou, Haibo Mei, Vadim A. Soloshonok, Jianlin Han, Yi Pan

J. Fluor. Chem. 2015, v.170, pp 5765

N

R R

H

F3C NS

O

N

R

R

H

NH

S

OCF3BF3 EtO2(100 mol %)

CH2Cl2, 10 h

-780C to rt

Synthesis of (2S,3S)-b-(trifluoromethyl)-a,b-diamino acid by Mannich addition of glycine Schiff base Ni(II) complexes to N-tert-butylsulfinyl-

3,3,3-trifluoroacetaldimine

Akie Kawamura, Hiroki Moriwaki, Gerd-Volker Roschenthaler, Kosuke Kawada, Jose Luis Acena, Vadim A. Soloshonok

J. Fluor. Chem. 2015, v.171, pp 6772

F3C NS

O

Ph

Ph

N CO2R

(Ss)

NH

S

OCF3

RO2C

NPh

Ph (2S,3S)(Ss)

F3CCO2H

NH2

NH2

(2S,3S)

Cs2CO3(10 mol%)

THF, rt

89-98%

Brsted acid-catalyzed electrophilic trifluoromethylthiolation of indoles using thermally stable trifluoromethylthiolating reagent

Bingqing Ma, Xinxin Shao, Qilong Shen

J. Fluor. Chem. 2015, v.171, pp 7377

N

R1

R2ClCH2CH2Cl

400C, 20-48 h

Ar

Me

Me

OSCF3N

R1

R2

Ar= 2-iodophenyl

SCF3

CSA (10 mol%)

Reactions of organozinc reagents with potassium bromodifluoroacetate

Vitalij V. Levin, Artem A. Zemtsov, Marina I. Struchkova, Alexander D. Dilman

J. Fluor. Chem. 2015, v.171, pp 97101

Ph ZnBrrt, 20 h

Br

F F

O

OK

Ph

F F

ZnBrPh

F

F

AcOH

DMF, 500C

Synthesis of tetrafluoroethyl- and tetrafluoroethylene-containing amines by the reaction of silanes with enamines under acidic

conditions

Yana Chernykh, Bronislav Jura sek, Petr Beier

J. Fluor. Chem. 2015, v.171, pp 162168

DMF, -500C to rtBrCF2CF2Br

PhSH, NaHPhSCF2CF2Br

Mg, Me3SiCl

THF, -780C to rtPhSCF2CF2SiMe3 PhSO2CF2CF2SiMe3

m-CPBA

CH2Cl200C to rt

30% H2O2

AcOH, 600C

64%

90% 92%91%

S

O

N4-Tol Ph

S

O

NH

*

Ph

CF2CF2SPh

4-TolPhSCF2CF2SiMe3

OAc (1 equiv.)

DMF, -400C, 2 h

20%(2 equiv.)

dr 83:17

n-Bu4N