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
[81]   Versatile Enantioselective Synthesis of Functionalized Lactones via Copper-Catalyzed Radical Oxyfunctionalization of Alkenes [J].
Zhu, Rong ;
Buchwald, Stephen L. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (25) :8069-8077