Metal-Free Direct Trifluoromethylation of Activated Alkenes with Langlois' Reagent Leading to CF3-Containing Oxindoles

被引：131
作者：
Wei, Wei
Wen, Jiangwei
Yang, Daoshan
Liu, Xiaoxia
Guo, Mengyuan
Dong, Ruimei
Wang, Hua [1 ]
机构：
[1] Qufu Normal Univ, Sch Chem & Chem Engn, Key Lab Life Organ Anal, Qufu 273165, Shandong, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 09期
基金：
中国国家自然科学基金;
关键词：
COPPER-CATALYZED TRIFLUOROMETHYLATION; N-ARYL ACRYLAMIDES; BOND FORMATION; FLUORINE; ACIDS; ARYLTRIFLUOROMETHYLATION; FUNCTIONALIZATION; EFFICIENT; BEARING;
D O I：
10.1021/jo500515x
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A metal-free and cost-effective synthesis protocol has been initially proposed for the construction of CF3-containing oxindoles via the direct oxidative trifluoromethylation of activated alkenes with Langlois' reagent (CF3SO2Na). The present methodology, which utilizes very cheap CF3 reagent and a simple oxidant, provides a convenient and practical approach to CF3-containing oxindoles with a wide variety of functional groups.
引用
收藏
页码：4225 / 4230
页数：6
相关论文
共 51 条
[1]   Reactive spin state dependent enantiospecific photocyclization of axially chiral α-substituted acrylanilides [J].
Ayitou, Anoklase Jean-Luc ;
Sivaguru, J. .
CHEMICAL COMMUNICATIONS, 2011, 47 (09) :2568-2570
[2]  
Banks R. E., 1994, ORGANALLUORINE CHEMI
[3]   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
[4]   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-+
[5]   Oxidative Trifluoromethylation of Unactivated Olefins: An Efficient and Practical Synthesis of α-Trifluoromethyl-Substituted Ketones [J].
Deb, Arghya ;
Manna, Srimanta ;
Modak, Atanu ;
Patra, Tuhin ;
Maity, Soham ;
Maiti, Debabrata .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (37) :9747-9750
[6]   Active trifluoromethylating agents from well-defined copper(I)-CF3 complexes [J].
Dubinina, Galyna G. ;
Furutachi, Hideki ;
Vicic, David A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (27) :8600-+
[7]   Concise synthesis of oxindole derivatives bearing a 3-trifluoroethyl group: Copper-catalyzed trifluoromethylation of acryloanilides [J].
Egami, Hiromichi ;
Shimizu, Ryo ;
Sodeoka, Mikiko .
JOURNAL OF FLUORINE CHEMISTRY, 2013, 152 :51-55
[8]   Trifluoromethylation Reactions for the Synthesis of β-Trifluoromethylamines [J].
Egami, Hiromichi ;
Kawamura, Shintaro ;
Miyazaki, Ayako ;
Sodeoka, Mikiko .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (30) :7841-7844
[9]   Alkene Trifluoromethylation Coupled with CC Bond Formation: Construction of Trifluoromethylated Carbocycles and Heterocycles [J].
Egami, Hiromichi ;
Shimizu, Ryo ;
Kawamura, Shintaro ;
Sodeoka, Mikiko .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (14) :4000-4003
[10]  
Furuya T, 2008, CURR OPIN DRUG DISC, V11, P803
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