Visible-light-induced thiotrifluoromethylation of terminal alkenes with sodium triflinate and benzenesulfonothioates

被引:70
作者
Kong, Weiguang [1 ]
An, Hejun [1 ]
Song, Qiuling [1 ]
机构
[1] Huaqiao Univ, Coll Mat Sci & Engn, Coll Chem Engn, Inst Next Generat Matter Transformat, 668 Jimei Blvd, Xiamen 361021, Fujian, Peoples R China
关键词
ALIPHATIC CARBOXYLIC-ACIDS; CARBON MULTIPLE BONDS; PHOTOREDOX CATALYSIS; UNACTIVATED ALKENES; DIASTEREOSELECTIVE SYNTHESIS; TRIFLUOROMETHYLATION REACTIONS; VICINAL DIFUNCTIONALIZATION; ORGANIC-SYNTHESIS; ELECTRON-TRANSFER; HIGHLY EFFICIENT;
D O I
10.1039/c7cc03520a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An unconventional reductive quenching cycle was developed to realize the visible-light-induced thiotrifluoromethylation of terminal alkenes. CF(3)SO(2)Nawas used as an easy tohandleCF(3) radical source to afford the desired products in moderate to good yields. Mild reaction conditions and a broad substrate scope feature in this transformation.
引用
收藏
页码:8968 / 8971
页数:4
相关论文
共 79 条
[1]   Carbon Trifluoromethylation Reactions of Hydrocarbon Derivatives and Heteroarenes [J].
Alonso, Concepcion ;
Martinez de Marigorta, Eduardo ;
Rubiales, Gloria ;
Palacios, Francisco .
CHEMICAL REVIEWS, 2015, 115 (04) :1847-1935
[2]   Visible Light Photocatalysis for the Generation and Use of Reactive Azolyl and Polyfluoroaryl Intermediates [J].
Arora, Amandeep ;
Weaver, Jimmie D. .
ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (10) :2273-2283
[3]   Trifluoromethylchlorosulfonylation of Alkenes: Evidence for an Inner-Sphere Mechanism by a Copper Phenanthroline Photoredox Catalyst [J].
Bagal, Dattatraya B. ;
Kachkovskyi, Georgiy ;
Knorn, Matthias ;
Rawner, Thomas ;
Bhanage, Bhalchandra M. ;
Reiser, Oliver .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (24) :6999-7002
[4]   Catalytic, Diastereoselective 1,2-Difluorination of Alkenes [J].
Banik, Steven M. ;
Medley, Jonathan William ;
Jacobsen, Eric N. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (15) :5000-5003
[5]  
Cardona F, 2009, NAT CHEM, V1, P269, DOI [10.1038/nchem.256, 10.1038/NCHEM.256]
[6]  
Ceroni P., 2012, LECT NOTES CHEM, V78, P74
[7]   Controlled Fluoroalkylation Reactions by Visible-Light Photoredox Catalysis [J].
Chatterjee, Tanmay ;
Iqbal, Naeem ;
You, Youngmin ;
Cho, Eun Jin .
ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (10) :2284-2294
[8]   v Catalytic Aminohalogenation of Alkenes and Alkynes [J].
Chemler, Sherry R. ;
Bovino, Michael T. .
ACS CATALYSIS, 2013, 3 (06) :1076-1091
[9]   Characterizing chain processes in visible light photoredox catalysis [J].
Cismesia, Megan A. ;
Yoon, Tehshik P. .
CHEMICAL SCIENCE, 2015, 6 (10) :5426-5434
[10]   Visible-light-induced photocatalytic oxytrifluoromethylation of N-allylamides for the synthesis of CF3-containing oxazolines and benzoxazines [J].
Deng, Qiao-Hui ;
Chen, Jia-Rong ;
Wei, Qiang ;
Zhao, Quan-Qing ;
Lu, Liang-Qiu ;
Xiao, Wen-Jing .
CHEMICAL COMMUNICATIONS, 2015, 51 (17) :3537-3540