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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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-11-11
DOI
https://doi.org/10.1021/acs.joc.6c02486
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
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article

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

Xiaoan Wen, Haoliang Yuan, Qing‐Long Xu, Tang Hua-jian et al.
The Journal of Organic Chemistry
Sulfur-Based Synthesis Techniques
article

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

Xiaoan Wen, Haoliang Yuan, Qing‐Long Xu, Tang Hua-jian, Chaoxin Wang, Liu Liu, Li-Na Qian, Jian-Kang Sun
article en

Abstract

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.

The Journal of Organic Chemistry
China Pharmaceutical University (CN)
Sulfur-Based Synthesis Techniques
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