N,N-Dimethyl-S-difluoromethyl-S-phenylsulfoximinium tetrafluoroborate: A versatile electrophilic difluoromethylating reagent

Over the past decade, sulfur-based fluoromethyl containing compounds have been exhaustively investigated as versatile fluoroalkylating reagents by our research laboratory as well as many others. Lately, we have designed a novel electrophilic difluoromethylating protocol employing in situ prepared N,N-dimethyl-S-difluoromethyl-S-phenylsulfoximinium salt. The present reagent provides excellent reactivity toward a broad spectrum of nucleophilic species (N-, P-, S-, and O-nucleophiles) to yield the corresponding difluoromethylated products with high efficacy under mild conditions. Additional studies have been performed to elucidate the mechanistic fundamentals of the reactions.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► N,N-Dimethyl-S-difluoromethyl-S-phenylsulfoximinium tetrafluoroborate is prepared. ► The reagent is able to difluoromethylate a series of P-, N, O-, and S-nucleophiles. ► Isotope labeling experiments were performed to investigate the mechanism. ► These studies indicate the compounds as an electrophilic difluoromethylating reagent.