Nucleophilic, radical, and electrophilic (phenylsulfonyl)difluoromethylations

Abstract

Selective incorporation of a fluoroalkyl moiety to modulate the properties of an organic molecule has become a frequently used strategy in life science- and materials science-related applications. In this context, selective introduction of a (phenylsulfonyl)difluoromethyl group (PhSO 2CF 2) into organic molecules has attracted much attention, since the PhSO 2CF 2 group can be regarded as a “chemical chameleon” that can be readily transformed into difluoromethyl (CF 2H), difluoromethylene (–CF 2–), and difluoromethylidene ( CF 2) functionalities. This article overviews the recent development of (phenylsulfonyl)difluoromethylation reactions from 2003, including the nucleophilic (phenylsulfonyl)difluoromethylations with PhSO 2CF 2H, PhSO 2CF 2SiMe 3 and PhSO 2CF 2Br reagents, free radical (phenylsulfonyl)difluoromethylations with PhSO 2CF 2I reagent, and electrophilic (phenylsulfonyl)difluoromethylations with a hypervalent iodine(III)-CF 2SO 2Ph reagent.