Intermolecular addition reactions of N-alkyl-N-chlorosulfonamides to unsaturated compounds

Abstract

N-Alkyl-N-chlorosulfonamides add to alkenes under copper(I) catalysis. In reactions of styrene derivatives with terminal double bonds the addition products were obtained in excellent yield and high regioselectivity. Lower yields are obtained in addition reactions to non-aromatic alkenes. The reaction most likely proceeds via a redox catalysis and amidyl radicals, a concerted mechanism has been ruled out and a polar mechanism via chloronium ions would lead to the opposite regiochemistry.

Keywords

• addition reactions
• catalysis
• N-chlorosulfonamides
• haloamination
• radical reaction