A simple protocol for stereoselective construction of novel β-sulfanyl vinyl sulfonyl fluorides

Abstract

The addition of thiols to 2-bromoprop-2-ene-1-sulfonyl fluoride (BPESF) in the presence of an organic base has been successfully employed for the synthesis of highly functionalized sulfanyl vinyl sulfonyl fluorides. This reaction features a broad substrate scope, mild reaction conditions, high atom economy, good to excellent isolated yields of up to 100%, and remarkable stereoselectivity, making it valuable for applications in chemical biology and medicinal chemistry. Further product diversification resulted in the construction of enaminyl sulfonyl fluorides.