Disruption of p−π Conjugation Enables Halonium-Mediated Dearomative Difunctionalization of Benzothiophenes

Organic Letters 2026

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Authors: Xian-Yan Shen, Jing-Yu Yan, Ji‐Rong Huang
DOI: 10.1021/acs.orglett.6c00207
Cited by: 1
References: 46

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.

Fields of Study & Subjects

Catalytic C–H Functionalization Methods Radical Photochemical Reactions Catalytic Cross-Coupling Reactions

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
9
Pages
2959–2964
Publication date
19 February 2026
Language
EN