Nucleophilic, radical, and electrophilic (phenylsulfonyl)difluoromethylations

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 (PhSO2CF2) into organic molecules has attracted much attention, since the PhSO2CF2 group can be regarded as a chemical chameleon that can be readily transformed into difluoromethyl (CF2H), difluoromethylene (-CF2-), and difluoromethylidene (=CF2) functionalities. This article overviews the recent development of (phenylsulfonyl)difluoromethylation reactions from 2003, including the nucleophilic (phenylsulfonyl)difluoromethylations with PhSO2CF2H, PhSO2CF2SiMe3 and PhSO2CF2Br reagents, free radical (phenylsulfonyl)difluoromethylations with PhSO(2)CF(2)l reagent. and electrophilic (phenylsulfonyl)difluoromethylations with a hypervalent iodine(III)-CF2SO2Ph reagent. (C) 2009 Elsevier B.V. All rights reserved.