Deaminative Radical Sulfinylation Reaction

Abstract

A straightforward and efficient deaminative radical sulfinylation of primary amines has been established for the facile synthesis of structurally diverse sulfinamides. This transformation exploits commercially accessible O-diphenylphosphinylhydroxylamine (DPPH) as a mild activator, enabling readily available alkyl and aryl primary amines to serve as versatile radical precursors. These radical species efficiently couple with electrophilic sulfinylamine partners to furnish a broad spectrum of alkyl and aryl sulfinamides in generally moderate to good yields. The synthetic robustness and generality of this protocol are further demonstrated by late-stage functionalization of various pharmaceutical scaffolds, scalable synthesis, and diversified downstream derivatization of the obtained sulfinamide products. Mechanistic studies corroborate a radical addition pathway as the plausible reaction mechanism underlying this deaminative transformation.