Oxidative Trifluoromethylation of Unactivated Olefins: An Efficient and Practical Synthesis of α-Trifluoromethyl-Substituted Ketones

被引：272

作者：

Deb, Arghya ^{[1
]}

Manna, Srimanta ^{[1
]}

Modak, Atanu ^{[1
]}

Patra, Tuhin ^{[1
]}

Maity, Soham ^{[1
]}

Maiti, Debabrata ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 37期

关键词：

ketones; Langlois reagent; olefins; synthetic methods; trifluoromethylation; SILYL ENOL ETHERS; RADICAL TRIFLUOROMETHYLATION; MEDICINAL CHEMISTRY; CARBONYL-COMPOUNDS; SODIUM TRIFLUOROMETHANESULFINATE; ASYMMETRIC TRIFLUOROMETHYLATION; CATALYZED TRIFLUOROMETHYLATION; MEDIATED TRIFLUOROMETHYLATION; PHOTOREDOX CATALYSIS; AROMATIC-COMPOUNDS;

D O I：

10.1002/anie.201303576

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An economical approach to α-CF3-substituted ketones, which are important intermediates in synthetic and medicinal chemistry, employs olefins and the readily available Langlois reagent (CF3SO 2Na). The reaction is operationally simple, proceeds at room temperature, and exhibits an excellent tolerance toward a wide variety of functional groups. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：9747 / 9750

页数：4

共 68 条

[61] Recent Developments on the Trifluoromethylation of (Hetero)Arenes
Wu, Xiao-Feng
Neumann, Helfried
Beller, Matthias
[J]. CHEMISTRY-AN ASIAN JOURNAL, 2012, 7 (08) : 1744 - 1754
[62] Copper-catalyzed trifluoromethylation of aryl boronic acids using a CF3+ reagent
Xu, Jun
Luo, Dong-Fen
Xiao, Bin
Liu, Zhao-Jing
Gong, Tian-Jun
Fu, Yao
Liu, Lei
[J]. CHEMICAL COMMUNICATIONS, 2011, 47 (14) : 4300 - 4302
[63] Practical Method for the Cu-Mediated Trifluoromethylation of Arylboronic Acids with CF3 Radicals Derived from NaSO2CF3 and tert-Butyl Hydroperoxide (TBHP)
Ye, Yingda
Kuenzi, Stefan A.
Sanford, Melanie S.
[J]. ORGANIC LETTERS, 2012, 14 (19) : 4979 - 4981
[64] Direct Cupration of Fluoroform
Zanardi, Alessandro
Novikov, Maxim A.
Martin, Eddy
Benet-Buchholz, Jordi
Grushin, Vladimir V.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (51) : 20901 - 20913
[65] Zhang C.-P., 2011, Angew. Chem, V123, P1936
[66] Progress in fluoroalkylation of organic compounds via sulfinatodehalogenation initiation system
Zhang, Cheng-Pan
Chen, Qing-Yun
Guo, Yong
Xiao, Ji-Chang
Gu, Yu-Cheng
[J]. CHEMICAL SOCIETY REVIEWS, 2012, 41 (12) : 4536 - 4559
[67] Copper-Mediated Trifluoromethylation of Heteroaromatic Compounds by Trifluoromethyl Sulfonium Salts
Zhang, Cheng-Pan
Wang, Zong-Ling
Chen, Qing-Yun
Zhang, Chun-Tao
Gu, Yu-Cheng
Xiao, Ji-Chang
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (08) : 1896 - 1900
[68] Generation of the CF3 radical from trifluoromethylsulfonium triflate and its trifluoromethylation of styrenes
Zhang, Cheng-Pan
Wang, Zong-Ling
Chen, Qing-Yun
Zhang, Chun-Tao
Gu, Yu-Cheng
Xiao, Ji-Chang
[J]. CHEMICAL COMMUNICATIONS, 2011, 47 (23) : 6632 - 6634

← 1 2 3 4 5 6 7 →