Copper-Mediated Trifluoromethylation of Heteroaromatic Compounds by Trifluoromethyl Sulfonium Salts

被引：270

作者：

Zhang, Cheng-Pan ^{[1
]}

Wang, Zong-Ling ^{[2
]}

Chen, Qing-Yun ^{[1
]}

Zhang, Chun-Tao ^{[2
]}

Gu, Yu-Cheng ^{[3
]}

Xiao, Ji-Chang ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China

[2] Hunan Univ Chinese Med, Changsha 410208, Hunan, Peoples R China

[3] Jealotts Hill Int Res Ctr, Bracknell RG42 6EY, Berks, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 08期

关键词：

copper; fluorine; heterocycles; sulfonium salts; trifluoromethylation; MILD ELECTROPHILIC TRIFLUOROMETHYLATION; MEDICINAL CHEMISTRY; AROMATIC-COMPOUNDS; ARYL HALIDES; IN-SITU; AGENTS; REAGENTS; FLUORINE; IODINE; (TRIFLUOROMETHYL)COPPER;

D O I：

10.1002/anie.201006823

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Copper is king! A convenient method for the synthesis of trifluoromethylated heteroaromatic compounds under mild conditions has been developed based on the observation that 1 can be reduced by certain metals (see scheme). Substrate 1 is assumed to be reduced by copper via a single-electron transfer mechanism, and CuCF3 is the most probable intermediate in this reaction. DMF=N,N-dimethylformamide, Tf=triflate. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：1896 / 1900

页数：5

共 60 条

[1] Adamczewski M., 2010, PCT Int. Appl., Patent No. [2010012793, WO 2010/012793]
[2] [Anonymous], 2005, ANGEW CHEM
[3] [Anonymous], 2009, Angew. Chem., Int. Ed.
[4] Sodium trifluoroacetate: an efficient precursor for the trifluoromethylation of aldehydes
Chang, Y
Cai, C
[J]. TETRAHEDRON LETTERS, 2005, 46 (18) : 3161 - 3164
[5] A NOVEL TRIFLUOROMETHYLATION METHOD OF SATURATED ORGANIC HALIDES
CHEN, QY
DUAN, JX
[J]. TETRAHEDRON LETTERS, 1993, 34 (26) : 4241 - 4244
[6] STUDIES ON FLUOROALKYLATION AND FLUOROALKOXYLATION .33. DIRECT TRIFLUOROMETHYLATION OF ARYL HALIDES WITH FLUOROSULPHONYLDIFLUOROMETHYL IODIDE IN THE PRESENCE OF COPPER - AN ELECTRON-TRANSFER INDUCED PROCESS
CHEN, QY
WU, SW
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (12): : 2385 - 2387
[7] CHEN QY, 1993, J CHEM SOC P1, V6, P645
[8] Cottet F, 2002, EUR J ORG CHEM, V2002, P327
[9] Active trifluoromethylating agents from well-defined copper(I)-CF3 complexes
Dubinina, Galyna G.
Furutachi, Hideki
Vicic, David A.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (27) : 8600 - +
[10] Novel 10-I-3 hypervalent iodine-based compounds for electrophilic trifluoromethylation
Eisenberger, P
Gischig, S
Togni, A
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (09) : 2579 - 2586

← 1 2 3 4 5 6 →