Thiourea/NCBSI/HCl System: Telescoping alkyl halide to alkyl sulfonyl chloride by recyclable N-chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI)

Abstract

A 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 via easy formation of S-alkyl isothiouronium salts using inexpensive thiourea. The mild reaction conditions and broad substrate scope make this method beneficial and advantageous to alkylsulfonyl chloride syntheses.