Disruption of p-π Conjugation Enables Halonium-Mediated Dearomative Difunctionalization of Benzothiophenes
Xian-Yan Shen1, Jing-Yu Yan1, Ji-Rong Huang1
1School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China.
Abstract:
p-π conjugation enriches electron density and facilitates the reactivity of adjacent π systems while simultaneously constraining electron mobility in subsequent transformations. Building on prior sulfur oxide chemistry, we leverage disruption of inherent p-π conjugation to enable halonium-mediated dearomative difunctionalization of benzothiophenes. As a result, mild dearomative difunctionalization converts planar benzothiophenes into structurally enriched three-dimensional counterparts, which can be further transformed into peripherally functionalized planar benzothiophene derivatives.
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