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Visible-Light-Mediated Late-Stage Sulfonylation of Boronic Acids via N–S Bond Activation of Sulfonamides

“…Sulfonamide groups are prevalent in diverse drugs and commercial chemicals . They are usually recognized as pharmacophores or protecting groups of amines; however, they rarely serve as a sulfonyl source because of the great challenge of cleaving N–S bonds in sulfonamides. , Compared with traditional sulfonylation reagents like sulfonyl chlorides, sulfinates, or sulfur dioxide, sulfonamides are stable, readily available, and able to survive under diverse reaction conditions, including transition metal-catalyzed cross-coupling, amide/ester formation, and nucleophilic alkylation reactions, which make sulfonamides good sulfonyl sources for the late-stage functionalization. In 2019, Fier and Maloney reported a mild method for generation of sulfinates from primary sulfonamides via NHC-catalyzed deamination of sulfonyl imines, which provided a simple and operational approach for functionalization of sulfonamide groups (Scheme a).…”