Copper-catalyzed trifluoromethylation of aryl boronic acids using a CF3+ reagent

被引：245

作者：

Xu, Jun

Luo, Dong-Fen

Xiao, Bin

Liu, Zhao-Jing

Gong, Tian-Jun

Fu, Yao

Liu, Lei ^{[1
]}

机构：

[1] Univ Sci & Technol China, Dept Chem, Hefei 230026, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2011年 / 47卷 / 14期

关键词：

ORGANIC HALIDES; FLUORINE; PERFLUOROALKYLATION; TEMPERATURE; BORYLATION; IODINE; AGENTS; ZINC; CU;

D O I：

10.1039/c1cc10359h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A copper-catalyzed process for trifluoromethylation of aryl, heteroaryl, and vinyl boronic acids has been developed. The reaction is conducted under mild conditions and shows tolerance to moisture and a variety of functional groups.

引用

页码：4300 / 4302

页数：3

共 40 条

[1] Aryl-CF3 Bond-Forming Reductive Elimination from Palladium(IV) [J].

Ball, Nicholas D. ;

Kampf, Jeff W. ;

Sanford, Melanie S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (09) :2878-+

[2]

BOSEWELL GA, 1974, ORG REACTIONS, V21, P1

[3] A REMARKABLY SIMPLE PREPARATION OF (TRIFLUOROMETHYL)CADMIUM AND (TRIFLUOROMETHYL) ZINC REAGENTS DIRECTLY FROM DIFLUORODIHALOMETHANES [J].

BURTON, DJ ;

WIEMERS, DM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (17) :5014-5015

[4] Direct observation of CuI/CuIII redox steps relevant to Ullmann-type coupling reactions [J].

Casitas, Alicia ;

King, Amanda E. ;

Parella, Teodor ;

Costas, Miquel ;

Stahl, Shannon S. ;

Ribas, Xavi .

CHEMICAL SCIENCE, 2010, 1 (03) :326-330

[5] The Palladium-Catalyzed Trifluoromethylation of Aryl Chlorides [J].

Cho, Eun Jin ;

Senecal, Todd D. ;

Kinzel, Tom ;

Zhang, Yong ;

Watson, Donald A. ;

Buchwald, Stephen L. .

SCIENCE, 2010, 328 (5986) :1679-1681

[6] Copper-Mediated Oxidative Trifluoromethylation of Boronic Acids [J].

Chu, Lingling ;

Qing, Feng-Ling .

ORGANIC LETTERS, 2010, 12 (21) :5060-5063

[7]

Cottet F, 2002, EUR J ORG CHEM, V2002, P327

[8] DFT studies on the borylation of α,β-unsaturated carbonyl compounds catalyzed by phosphine copper(I) boryl complexes and observations on the interconversions between O- and C-bound enolates of Cu, B, and Si [J].

Dang, Li ;

Lin, Zhenyang ;

Marder, Todd B. .

ORGANOMETALLICS, 2008, 27 (17) :4443-4454

[9] Active trifluoromethylating agents from well-defined copper(I)-CF3 complexes [J].

Dubinina, Galyna G. ;

Furutachi, Hideki ;

Vicic, David A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (27) :8600-+

[10] Structure of Bis(trifluoromethyl)cuprate and Its Role in Trifluoromethylation Reactions [J].

Dubinina, Galyna G. ;

Ogikubo, Junichi ;

Vicic, David A. .

ORGANOMETALLICS, 2008, 27 (23) :6233-6235

← 1 2 3 4 →