Switchable Divergent Reactions of α-Aryl Vinylsulfoniums with Benzothiophene-and Benzofuran-Based Aza-dienes

Abstract

A switchable divergent reaction of α-aryl vinylsulfoniums with benzothiophene-based aza-dienes is achieved by choosing commercially available bases and catalysts. This strategy enables the one-pot synthesis of sulfur-containing 6-5-6- and 6-5-5-fused tricyclic compounds, and benzothiophene and benzofuran derivatives. All target products were obtained in moderate to excellent isolated yields. The successful scale-up synthesis and further derivatizations highlight the potential synthetic utility of the developed methodology. Additionally, plausible reaction pathways are proposed based on experimental findings.