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

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...