Visible-light-mediated direct perfluoroalkylation and trifluoromethylation of free anilines

被引:20
作者
He, Chun-Yang [1 ]
Gu, Ji-Wei [2 ]
Zhang, Xingang [2 ]
机构
[1] Zunyi Med Univ, Sch Pharm, 6 West Xuefu Rd, Zunyi 563003, Guizhou, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, 345 Lingling Lu, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
Perfluoroalkylation; Trifluoromethylation; Anilines; Photoredox catalysis; Visible-light; MEDICINAL CHEMISTRY; PHOTOREDOX CATALYSIS; FLUORINE; ALKENES; ARENES; FLUOROALKYLATION; HETEROARENES; AROMATICS;
D O I
10.1016/j.tetlet.2017.09.010
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A mild, operationally simple method for direct perfluoroalkylation and trifluoromethylation of anilines through visible-light-mediated photoredox catalysis from broadly available perfluoroalkyl iodides and free anilines is described. The method provides a facile route for application in drug discovery and development. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3939 / 3941
页数:3
相关论文
共 35 条
[1]   Tamed Arene and Heteroarene Trifluoromethylation [J].
Besset, Tatiana ;
Schneider, Cedric ;
Cahard, Dominique .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (21) :5048-5050
[2]   STUDIES ON FLUOROALKYLATION AND FLUOROALKOXYLATION .28. PALLADIUM(O)-INDUCED ADDITION OF FLUOROALKYL IODIDES TO ALKENES - AN ELECTRON-TRANSFER PROCESS [J].
CHEN, QY ;
YANG, ZY ;
ZHAO, CX ;
QIU, ZM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (03) :563-567
[3]   A General Synthesis of Fluoroalkylated Alkenes by Palladium-Catalyzed Heck-Type Reaction of Fluoroalkyl Bromides [J].
Feng, Zhang ;
Min, Qiao-Qiao ;
Zhao, Hai-Yang ;
Gu, Ji-Wei ;
Zhang, Xingang .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (04) :1270-1274
[4]   The many roles for fluorine in medicinal chemistry [J].
Hagmann, William K. .
JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (15) :4359-4369
[5]   Transition metal catalysis and nucleophilic fluorination [J].
Hollingworth, Charlotte ;
Gouverneur, Veronique .
CHEMICAL COMMUNICATIONS, 2012, 48 (24) :2929-2942
[6]  
Huang W.-Y, 1992, CHINESE J CHEM, V10, P180
[7]  
Huang W.-Y., 1992, CHINESE J CHEM, V10, P373
[8]   Nickel(0)-catalyzed fluoroalkylation of alkenes, alkynes, and aromatics with perfluoroalkyl chlorides [J].
Huang, XT ;
Chen, QY .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (13) :4651-4656
[9]   Trifluoromethylation of heterocycles via visible light photoredox catalysis [J].
Iqbal, Naeem ;
Choi, Sungkyu ;
Ko, Euna ;
Cho, Eun Jin .
TETRAHEDRON LETTERS, 2012, 53 (15) :2005-2008
[10]   Photochemical Approaches to Complex Chemotypes: Applications in Natural Product Synthesis [J].
Karkas, Markus D. ;
Porco, John A., Jr. ;
Stephenson, Corey R. J. .
CHEMICAL REVIEWS, 2016, 116 (17) :9683-9747