Visible-Light Photoredox Decarboxylation of Perfluoroarene Iodine(III) Trifluoroacetates for C-H Trifluoromethylation of (Hetero)arenes

被引:117
作者
Yang, Bin [1 ]
Yu, Donghai [2 ]
Xu, Xiu-Hua [1 ]
Qing, Feng-Ling [1 ,3 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Ctr Excellence Mol Synth, Key Lab Organofluorine Chem, 345 Lingling Lu, Shanghai 200032, Peoples R China
[2] Donghua Univ, Coll Chem Chem Engn & Biotechnol, 2999 North Renmin Lu, Shanghai 201620, Peoples R China
[3] Hunan Normal Univ, Key Lab Chem Biol & Tradit Chinese Med Res, Minist Educ China, Coll Chem & Chem Engn, Changsha 410081, Hunan, Peoples R China
基金
中国国家自然科学基金;
关键词
trifluoromethylation; photocatalysis; decarboxylation; trifluoroacetic acid; iodine(III) reagent; ALPHA-OXOCARBOXYLIC ACIDS; AROMATIC-COMPOUNDS; CARBOXYLIC-ACIDS; KETO ACIDS; PERFLUOROALKYLATION; ALKENES; CATALYSIS; REAGENTS; FUNCTIONALIZATION; DRIVEN;
D O I
10.1021/acscatal.7b03990
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A scalable and operationally simple decarboxylative trifluoromethylation of (hetero)arenes with easily accessible C6F5I(OCOCF3)(2) under photoredox catalysis has been developed. This method is tolerant of various (hetero)-arenes and functional groups. Notably, C6F5I is recycled from the decarboxylation reaction and further used for the preparation of C6F5I(OCOCF3)(2). The combination of photoredox catalysis and hypervalent iodine reagent provides a practical approach for the application of trifluoroacetic acid in trifluoromethylation reactions.
引用
收藏
页码:2839 / 2843
页数:9
相关论文
共 81 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]  
[Anonymous], 2013, BEH
[3]   Difluoro- and Trifluoromethylation of Electron-Deficient Alkenes in an Electrochemical Microreactor [J].
Arai, Kenta ;
Watts, Kevin ;
Wirth, Thomas .
CHEMISTRYOPEN, 2014, 3 (01) :23-28
[4]   Photochemical Perfluoroalkylation with Pyridine N-Oxides: Mechanistic Insights and Performance on a Kilogram Scale [J].
Beatty, Joel W. ;
Douglas, James J. ;
Miller, Richard ;
McAtee, Rory C. ;
Cole, Kevin P. ;
Stephenson, Corey R. J. .
CHEM, 2016, 1 (03) :456-472
[5]   A scalable and operationally simple radical trifluoromethylation [J].
Beatty, Joel W. ;
Douglas, James J. ;
Cole, Kevin P. ;
Stephenson, Corey R. J. .
NATURE COMMUNICATIONS, 2015, 6
[6]   REACTIONS OF OLEFINIC DOUBLE-BONDS WITH POLYFLUOROALKYL RADICALS GENERATED ELECTROCHEMICALLY [J].
BROOKES, CJ ;
COE, PL ;
OWEN, DM ;
PEDLER, AE ;
TATLOW, JC .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1974, (09) :323-324
[7]   Electrophilic Trifluoromethylation by Use of Hypervalent Iodine Reagents [J].
Charpentier, Julie ;
Frueh, Natalja ;
Togni, Antonio .
CHEMICAL REVIEWS, 2015, 115 (02) :650-682
[8]   Rapid and Efficient Trifluoromethylation of Aromatic and Heteroaromatic Compounds Using Potassium Trifluoroacetate Enabled by a Flow System [J].
Chen, Mao ;
Buchwald, Stephen L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (44) :11628-11631
[9]   Radical-Mediated Fluoroalkylations [J].
Cho, Eun Jin .
CHEMICAL RECORD, 2016, 16 (01) :47-63
[10]   Oxidative Trifluoromethylation and Trifluoromethylthiolation Reactions Using (Trifluoromethyl)trimethylsilane as a Nucleophilic CF3 Source [J].
Chu, Lingling ;
Qing, Feng-Ling .
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (05) :1513-1522