Divergent Generation of the Difluoroalkyl Radical and Difluorocarbene via Selective Cleavage of C-S Bonds of the Sulfox-CF₂SO₂Ph Reagent

A new difluoroalkylation reagent Sulfox-CF2SO2Ph bearing both sulfoximine and sulfone moieties was prepared from commercially available SulfoxFluor and PhSO2CF2H. On one hand, the Sulfox-CF2SO2Ph reagent could act as a (phenylsulfonyl)difluoromethyl radical source under photoredox catalysis, in which the arylsulfoximidoyl group is selectively removed. On the other hand, under basic conditions, Sulfox-CF2SO2Ph could serve as a difluorocarbene precursor for S- and O-difluoromethylations with S- and O-nucleophiles, respectively, in which the phenylsulfonyl group in Sulfox-CF2SO2Ph is selectively removed (followed by alpha-elimination of the arylsulfoximidoyl group).