Palladium-Catalyzed Oxidative Synthesis of α-Acetoxylated Enones from Alkynes

Abstract

We report a palladium-catalyzed oxidative functionalization of alkynes to generate α-acetoxylated enones in one step. A range of functional groups are well-tolerated in this reaction. Mechanistic studies, including the use of 18O-labeled DMSO, revealed that the ketone oxygen atom in the product originates from DMSO. Combating oxygen deficiency: A one-step protocol has been developed for the palladium-catalyzed conversion of simple alkynes into α-acetoxylated enones under oxidative conditions (see scheme; BQ=1,4-benzoquinone). A wide range of functional groups are tolerated in the reaction. Mechanistic studies with [18O]DMSO revealed that the ketone oxygen atom in the product originates from DMSO.