Metal-Free Aryltrifluoromethylation of Activated Alkenes

被引：295
作者：
Kong, Wangqing [1 ]
Casimiro, Maria [1 ]
Fuentes, Noelia [1 ]
Merino, Estibaliz [1 ]
Nevado, Cristina [1 ]
机构：
[1] Univ Zurich, Inst Organ Chem, CH-8006 Zurich, Switzerland
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 49期
基金：
欧洲研究理事会;
关键词：
alkenes; arenes; iodine; Togni reagent; trifluoromethylation; COPPER-CATALYZED TRIFLUOROMETHYLATION; BOND FORMATION; ELECTROPHILIC TRIFLUOROMETHYLATION; FLUORINATION; OXINDOLES; ALCOHOLS; IODIDES; REAGENT; SULFUR;
D O I：
10.1002/anie.201307377
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Metal-free: The first metal-free aryltrifluoromethylation of activated alkenes has been developed. With this method, trifluoromethylated isoquinolinediones, spirobicycles, oxindoles, and α-aryl-β- trifluoromethylamides were obtained with high control of the regioselectivity. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：13086 / 13090
页数：5
相关论文
共 71 条
[1]   The Productive Merger of Iodonium Salts and Organocatalysis: A Non-photolytic Approach to the Enantioselective α-Trifluoromethylation of Aldehydes [J].
Allen, Anna E. ;
MacMillan, David W. C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (14) :4986-+
[2]  
[Anonymous], 2009, Angew. Chem., Int. Ed.
[3]   Catalytic direct arylation with aryl chlorides, bromides, and iodides: Intramolecular studies leading to new intermolecular reactions [J].
Campeau, LC ;
Parisien, M ;
Jean, A ;
Fagnou, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (02) :581-590
[4]   SYNTHESIS OF PHOSPHALILOLIDINE AND PHOSPHAJULOLIDINE [J].
CHEN, CH ;
BRIGHTY, KE ;
MICHAELS, FM .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (02) :361-367
[5]   The Palladium-Catalyzed Trifluoromethylation of Aryl Chlorides [J].
Cho, Eun Jin ;
Senecal, Todd D. ;
Kinzel, Tom ;
Zhang, Yong ;
Watson, Donald A. ;
Buchwald, Stephen L. .
SCIENCE, 2010, 328 (5986) :1679-1681
[6]   Copper-Mediated Aerobic Oxidative Trifluoromethylation of Terminal Alkynes with Me3SiCF3 [J].
Chu, Lingling ;
Qing, Feng-Ling .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (21) :7262-+
[7]   Flexible Gold-Catalyzed Regioselective Oxidative Difunctionalization of Unactivated Alkenes [J].
de Haro, Teresa ;
Nevado, Cristina .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (04) :906-910
[8]  
deHaro T., 2011, ANGEW CHEM, V123, P936, DOI DOI 10.1002/ANGE.201005763
[9]  
Egami H., 2013, ANGEW CHEM, V125, P7995
[10]  
Egami H., 2013, ANGEW CHEM, V125, P4092
12345678