Silver-Mediated C-H Difluoromethylation of Arenes

• Published in: European journal of organic chemistry Vol. 2016; no. 28; pp. 4916 - 4921
• Main Authors: Li, Jialiang, Wan, Wen, Ma, Guobin, Chen, Yunrong, Hu, Qingyang, Kang, Kai, Jiang, Haizhen, Hao, Jian
• Format: Journal Article
• Language: English
• Published: WEINHEIM Blackwell Publishing Ltd 01.10.2016; Wiley; Wiley Subscription Services, Inc
• Subjects: Arenes; Chemistry; Chemistry, Organic; Fluorine; Physical Sciences; Radicals; Regioselectivity; Science & Technology; Silver; ROOM-TEMPERATURE; REAGENTS; Regioselectivity; Fluorine; FLUOROALKYLATION; Arenes; TRIFLUOROMETHYLATION REACTIONS; COPPER; Radicals; ARYLBORONIC ACIDS; Silver; HETEROARENES; ARYL BORONIC ACIDS; CATALYZED DIFLUOROMETHYLATION; GEM-DIFLUOROMETHYLENATION
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201600770

The first AgI‐mediated C–H ethoxycarbonyl difluoromethylation with TMSCF2COOEt (TMS = trimethylsilyl) has been developed. The radical difluoromethylation proceeds smoothly to give the difluoromethylated arenes in moderate to high yields with Friedel–Crafts‐type regioselectivity. Mechanistic studies indicate that the innate C–H difluoromethylation proceeds through an electrophilic radical‐type pathway. The first AgI‐mediated C–H difluoromethylation of arenes has been developed through an electrophilic radical‐type pathway.