Copper-Catalyzed Nucleophilic Trifluoromethylation of Allylic Halides: A Simple Approach to Allylic Trifluoromethylation

被引：61
作者：
Miyake, Yoshihiro [1 ]
Ota, Shin-ichi [1 ]
Nishibayashi, Yoshiaki [1 ]
机构：
[1] Univ Tokyo, Sch Engn, Inst Engn Innovat, Bunkyo Ku, Tokyo 1138656, Japan
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2012年 / 18卷 / 42期
关键词：
allylic compounds; copper; fluorine; homogeneous catalysis; trifluoromethylation; PD(II)-CATALYZED ORTHO-TRIFLUOROMETHYLATION; OXIDATIVE TRIFLUOROMETHYLATION; CONJUGATE ADDITION; ORGANIC-COMPOUNDS; TERMINAL ALKENES; BOND-FORMATION; BORONIC ACIDS; ARENES; PERFLUOROALKYLATION; ARYL;
D O I：
10.1002/chem.201202853
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Trifluoromethylation: The treatment of allylic halides with trifluoromethyltrimethylsilane in the presence of a catalytic amount of copper(I) thiophene-2-carboxylate (CuTC) gives the corresponding allylic trifluoromethylation products in good to high yields and with complete regioselectivity (see scheme). The use of THF as a solvent is crucial for obtaining good yields of product. © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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页码：13255 / 13258
页数：4
相关论文
共 94 条
[1]   Enantioselective copper-catalyzed conjugate addition and allylic substitution reactions [J].
Alexakis, A. ;
Backvall, J. E. ;
Krause, N. ;
Pamies, O. ;
Dieguez, M. .
CHEMICAL REVIEWS, 2008, 108 (08) :2796-2823
[2]  
[Anonymous], 2012, ANGEW CHEM INT ED, V51, P4577
[3]  
[Anonymous], 2012, ANGEW CHEM INT ED, V51, P5048
[4]  
[Anonymous], 2012, ANGEW CHEM INT ED, V51, P3713
[5]  
[Anonymous], 2012, ANGEW CHEM INT ED, V51, P1055
[6]  
[Anonymous], 2012, ANGEW CHEM INT ED, V51, P2947
[7]  
[Anonymous], 2009, ANGEW CHEM INT ED, V48, P4332
[8]  
[Anonymous], 2011, ANGEW CHEM INT ED, V50, P1896
[9]  
[Anonymous], 2011, ANGEW CHEM INT ED, V50, P1059
[10]  
[Anonymous], 2005, ANGEW CHEM
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