Chloride Induced S–C bond selective cleavage of disulfides to access unsymmetrical β-fluorodisulfides

Abstract

Selective S–C bond cleavage of disulfides presents a significant challenge due to the fact that S–S bonds are weaker than S–C bonds. In this study, we present a novel chloride-induced Selectfluor radical cation process for converting readily available symmetrical disulfides into unsymmetrical β-fluorodisulfides through selective S–C bond cleavage. Mechanistic investigations and DFT calculations suggest the involvement of a chlorinated disulfide radical, which subsequently reacts with alkenes to form β-fluorodisulfides via the atom transfer radical addition (ATRA) mechanism. Furthermore, this method exhibits broad functional group tolerance, enabling the synthesis of various target products in moderate to good yields.