Synthesis of Phenyl Sulfoxides via a Domino Electrophilic Sulfenylation/[2,3]-Sigmatropic Rearrangement/Aromatization Sequence of para-Quinols.

Abstract

[2, 3]-Sigmatropic rearrangement reactions have attracted considerable attention in organic synthesis as a powerful tool for constructing complex molecular frameworks. Herein, we report a novel domino process involving sulfenylation, [2, 3]-sigmatropic rearrangement and aromatization of para-quinols with electrophilic sulfur reagents, enabling the facile synthesis of substituted phenyl sulfoxides. This transformation proceeds efficiently under catalyst-free conditions at room temperature without the need for inert gas protection, affording the desired products in high yields. This protocol is characterized by mild reaction conditions, operational simplicity and broad substrate scope, thus offering a practical and versatile strategy for accessing diverse functionalized phenyl sulfoxides.

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