Intramolecular Acyl-Migration for Acyloxyselenenylation of Alkenes Promoted by Oxone

Abstract

A novel green methodology for the Oxone-mediated oxidative addition of alkenes via intramolecular acyl migration has been developed. This transformation utilizes N-acyl-N-sulfonyl allylamines and diselenides as starting materials, with Oxone serving as the oxidant and water as a partial oxygen source. The protocol enables the synthesis of a series of β-acyloxy-γ-selenyl sulfonamides with high to excellent yields and demonstrates broad substrate scope. Notably, the excellent yield was maintained in gram-scale experiments, highlighting the scalability of this method. Through comprehensive control experiments, we have elucidated the reaction mechanism, which involves rapid radical generation, a predominant cationic pathway, and intramolecular acyl migration. This study presents an efficient and environmentally benign approach to the synthesis of valuable β-acyloxy-γ-selenyl sulfonamides.