Silver-Catalyzed Hydrotrifluoromethylation of Unactivated Alkenes with CF3SiMe3

被引：249

作者：

Wu, Xinyue ^{[1
]}

Chu, Lingling ^{[1
]}

Qing, Feng-Ling ^{[1
,2
]}

机构：

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

[2] Donghua Univ, Coll Chem Chem Engn & Biotechnol, Shanghai 201620, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 08期

基金：

中国国家自然科学基金;

关键词：

fluorine; homogeneous catalysis; radical reactions; silver; synthetic methods; PD(II)-CATALYZED ORTHO-TRIFLUOROMETHYLATION; COPPER-MEDIATED TRIFLUOROMETHYLATION; ARYL BORONIC ACIDS; OXIDATIVE TRIFLUOROMETHYLATION; ROOM-TEMPERATURE; BOND-FORMATION; ALLYLIC TRIFLUOROMETHYLATION; REDUCTIVE ELIMINATION; ARYLBORONIC ACIDS; TERMINAL ALKENES;

D O I：

10.1002/anie.201208971

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A silver bullet: The title reaction results in selective formation of trifluoromethylated alkanes, and is in contrast to the previously reported transition-metal-catalyzed trifluoromethylation of olefins to generate a series of trifluoromethylated allylic compounds. Preliminary mechanistic investigations indicate that the current hydrotrifluoromethylation proceeds through a pathway involving a CF3 radical species. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：2198 / 2202

页数：5

共 108 条

[91] Ag-mediated reactions: Coupling and heterocyclization reactions
Weibel, Jean-Marc
Blanc, Aurelien
Pale, Patrick
[J]. CHEMICAL REVIEWS, 2008, 108 (08) : 3149 - 3173
[92] Cooperative Effect of Silver in Copper-Catalyzed Trifluoromethylation of Aryl Iodides Using Me3SiCF3
Weng, Zhiqiang
Lee, Richmond
Jia, Weiguo
Yuan, Yaofeng
Wang, Wenfeng
Feng, Xue
Huang, Kuo-Wei
[J]. ORGANOMETALLICS, 2011, 30 (11) : 3229 - 3232
[93] 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
[94] Copper-Catalyzed Trifluoromethylation of Terminal Alkenes through Allylic C-H Bond Activation
Xu, Jun
Fu, Yao
Luo, Dong-Fen
Jiang, Yuan-Ye
Xiao, Bin
Liu, Zhao-Jing
Gong, Tian-Jun
Liu, Lei
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (39) : 15300 - 15303
[95] 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
[96] Silver-Catalyzed Fluorination Reactions
Xu, Tao
Liu, Guosheng
[J]. SYNLETT, 2012, (07) : 955 - 958
[97] Three-component Oxytrifluoromethylation of Alkenes: Highly Efficient and Regioselective Difunctionalization of C=C Bonds Mediated by Photoredox Catalysts
Yasu, Yusuke
Koike, Takashi
Akita, Munetaka
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (38) : 9567 - 9571
[98] Ye Y., 2012, SYNLETT, P2005
[99] 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
[100] Merging Visible-Light Photocatalysis and Transition-Metal Catalysis in the Copper-Catalyzed Trifluoromethylation of Boronic Acids with CF3I
Ye, Yingda
Sanford, Melanie S.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (22) : 9034 - 9037

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