Reactivity of hypervalent iodine(III) reagents bearing a benzylamine with sulfenate salts

Abstract

The reactivity of our recently disclosed hypervalent iodine reagents (HIRs) bearing a benzylamine with in situ-generated sulfenate salts was investigated. Under the studied conditions sulfonamides have been obtained in up to 52% yield. This reaction has been extended to a variety of HIRs and sulfenate salts to explore the different reactivity of these new reagents. A plausible mechanism is proposed, suggesting a possible radical pathway.

Keywords

• electrophilic amination
• hypervalent iodine reagents
• sulfinamide
• sulfonamide