Palladium-catalyzed migratory allylic sulfonylation of allylic alcohols using sulfonyl hydrazides

Abstract

The unique electronic properties of the sulfonyl group make allylic sulfones particularly valuable as synthetic intermediates in organic chemistry. Their relevance could also be reflected by the fact that allylic sulfones are ubiquitous moieties in bioactive compounds and functional materials. Herein, we report an efficient palladium-catalyzed allylic migration strategy for the synthesis of allylic sulfones with good chemo- and regioselectivity under mild conditions. In this way, a broad range of allylic sulfone derivatives were achieved from the reaction of allylic alcohols with sulfonyl hydrazides in moderate to good yields, demonstrating the versatility and synthetic utility of this protocol. The implementation of the migration strategy stems from the migration process of the π-allylpalladium species, consisting of β-H elimination and migratory insertion processes.