Thiourea/NCBSI/HCl System: Telescoping Alkyl Halide to Alkyl Sulfonyl Chloride by Recyclable N-Chloro-N-(phenylsulfonyl)benzene Sulfonamide (NCBSI)

Abstract

AbstractA convenient and efficient method to synthesize diverse alkyl sulfonyl chlorides through N-chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI)-mediated oxidative chlorosulfonation of S-alkyl isothiouronium salts obtained from alkyl chlorides is presented. Synthesizing structurally diverse alkyl sulfonyl chloride in moderate to excellent yields up to 98% from alkyl halide was achieved via easy formation of S-alkyl isothiouronium salts using inexpensive thiourea. The mild reaction conditions and broad substrate scope make this method attractive for alkylsulfonyl chloride syntheses.