Trifluoromethylation Reactions for the Synthesis of β-Trifluoromethylamines

被引:179
作者
Egami, Hiromichi [1 ,2 ]
Kawamura, Shintaro [1 ,2 ]
Miyazaki, Ayako [1 ,2 ]
Sodeoka, Mikiko [1 ,2 ,3 ]
机构
[1] RIKEN, Synthet Organ Chem Lab, Wako, Saitama 3510198, Japan
[2] Japan Sci & Technol Agcy, Sodeoka Live Cell Chem Project, ERATO, Wako, Saitama 3510198, Japan
[3] RIKEN Ctr Sustainable Resource Sci, Wako, Saitama 3510198, Japan
关键词
amines; aziridines; copper; multicomponent reactions; trifluoromethylation; COPPER-CATALYZED TRIFLUOROMETHYLATION; PD(II)-CATALYZED ORTHO-TRIFLUOROMETHYLATION; ELECTROPHILIC TRIFLUOROMETHYLATION; TERMINAL ALKENES; FLUORINE; EFFICIENT; OXYTRIFLUOROMETHYLATION; HYDROTRIFLUOROMETHYLATION; ALLYLSILANES; REAGENTS;
D O I
10.1002/anie.201303350
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A multitalented system: N-Migratory oxytrifluoromethylation and one-pot three-component reactions of allylamines as well as the aminotrifluoromethylation of alkenyl amines all proceeded efficiently in the presence of the Togni reagent (1) and CuI to afford a variety of β-trifluoromethylamine derivatives (see scheme). Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:7841 / 7844
页数:4
相关论文
共 83 条
[71]  
Wu X., 2013, ANGEW CHEM, V125, P2254
[72]   Recent Developments on the Trifluoromethylation of (Hetero)Arenes [J].
Wu, Xiao-Feng ;
Neumann, Helfried ;
Beller, Matthias .
CHEMISTRY-AN ASIAN JOURNAL, 2012, 7 (08) :1744-1754
[73]   Silver-Catalyzed Hydrotrifluoromethylation of Unactivated Alkenes with CF3SiMe3 [J].
Wu, Xinyue ;
Chu, Lingling ;
Qing, Feng-Ling .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (08) :2198-2202
[74]   Copper-Catalyzed Trifluoromethylation of Terminal Alkenes through Allylic C-H Bond Activation [J].
Xu, Jun ;
Fu, Yao ;
Luo, Dong-Fen ;
Jiang, Yuan-Ye ;
Xiao, Bin ;
Liu, Zhao-Jing ;
Gong, Tian-Jun ;
Liu, Lei .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (39) :15300-15303
[75]   Radical-mediated hydroxytrifluoromethylation of α,β-unsaturated esters [J].
Yajima, T ;
Nagano, H ;
Saito, C .
TETRAHEDRON LETTERS, 2003, 44 (37) :7027-7029
[76]   Intermolecular Aminotrifluoromethylation of Alkenes by Visible-Light-Driven Photoredox Catalysis [J].
Yasu, Yusuke ;
Koike, Takashi ;
Akita, Munetaka .
ORGANIC LETTERS, 2013, 15 (09) :2136-2139
[77]   Three-component Oxytrifluoromethylation of Alkenes: Highly Efficient and Regioselective Difunctionalization of C=C Bonds Mediated by Photoredox Catalysts [J].
Yasu, Yusuke ;
Koike, Takashi ;
Akita, Munetaka .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (38) :9567-9571
[78]   Investigations into Transition-Metal-Catalyzed Arene Trifluoromethylation Reactions [J].
Ye, Yingda ;
Sanford, Melanie S. .
SYNLETT, 2012, (14) :2005-2013
[79]   Oxidation of a Cyclometalated Pd(II) Dimer with "CF3+": Formation and Reactivity of a Catalytically Competent Monomeric Pd(IV) Aquo Complex [J].
Ye, Yingda ;
Ball, Nicholas D. ;
Kampf, Jeff W. ;
Sanford, Melanie S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (41) :14682-14687
[80]   Generation of the CF3 radical from trifluoromethylsulfonium triflate and its trifluoromethylation of styrenes [J].
Zhang, Cheng-Pan ;
Wang, Zong-Ling ;
Chen, Qing-Yun ;
Zhang, Chun-Tao ;
Gu, Yu-Cheng ;
Xiao, Ji-Chang .
CHEMICAL COMMUNICATIONS, 2011, 47 (23) :6632-6634