Copper-Catalyzed Di- and Trifluoromethylation of α,β-Unsaturated Carboxylic Acids: A Protocol for Vinylic Fluoroalkylations

被引：224

作者：

He, Zhengbiao ^{[1
]}

Luo, Tao ^{[1
]}

Hu, Mingyou ^{[1
]}

Cao, Yanjing ^{[1
]}

Hu, Jinbo ^{[1
]}

机构：

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 16期

基金：

中国国家自然科学基金;

关键词：

carboxylic acids; copper; fluorine; stereoselectivity; synthetic methods; NUCLEOPHILIC TRIFLUOROMETHYLATION; BORONIC ACIDS; REAGENT; FLUORINE; ETHERS; ARYL; (PHENYLSULFONYL)DIFLUOROMETHYLATION; PERFLUOROALKYLATION; ALKENES; SALTS;

D O I：

10.1002/anie.201200140

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Dual action: The Lewis acid CuF 2·2 H 2O efficiently catalyzes the reaction between electrophilic fluoroalkylating agents and α,β-unsaturated carboxylic acids by dually activating both reactants, thus affording di- and trifluoromethyl alkenes in high yields with excellent E/Z selectivity. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：3944 / 3947

页数：4

共 48 条

[31] Parsons A. T., 2011, ANGEW CHEM, V123, P9286
[32] Copper-Catalyzed Trifluoromethylation of Unactivated Olefins
Parsons, Andrew T.
Buchwald, Stephen L.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (39) : 9120 - 9123
[33] Selective fluoroalkylations with fluorinated sulfones, sulfoxides, and Sulfides
Prakash, G. K. Surya
Hu, Jinbo
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2007, 40 (10) : 921 - 930
[34] Perfluoroalkylation with organosilicon reagents
Prakash, GKS
Yudin, AK
[J]. CHEMICAL REVIEWS, 1997, 97 (03) : 757 - 786
[35] Fluorine in medicinal chemistry
Purser, Sophie
Moore, Peter R.
Swallow, Steve
Gouverneur, Veronique
[J]. CHEMICAL SOCIETY REVIEWS, 2008, 37 (02) : 320 - 330
[36] Shelf-stable electrophilic trifluoromethylating reagents: A brief historical perspective
Shibata, Norio
Matsnev, Andrej
Cahard, Dominique
[J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2010, 6
[37] Modern synthetic methods for fluorine-substituted target molecules
Shimizu, M
Hiyama, T
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (02) : 214 - 231
[38] Nucleophilic trifluoromethylation reactions of organic compounds with (trifluoromethyl)trimethylsilane
Singh, RP
Shreeve, JM
[J]. TETRAHEDRON, 2000, 56 (39) : 7613 - 7632
[39] Aromatic Trifluoromethylation with Metal Complexes
Tomashenko, Olesya A.
Grushin, Vladimir V.
[J]. CHEMICAL REVIEWS, 2011, 111 (08) : 4475 - 4521
[40] Electrophilic perfluoroalkylating agents
Umemoto, T
[J]. CHEMICAL REVIEWS, 1996, 96 (05) : 1757 - 1777

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