Metal‐Free Synthesis of Oxindole‐Based Sulfones via 1,4‐Cyano Migration/Cyclization Through Radical SO <sub>2</sub> Insertion

Oxindole‐based sulfones are privileged structures found in bioactive compounds and natural products. Herein, a three‐component reaction of unactivated alkenes, potassium metabisulfite, and aryldiazonium tetrafluoroborates has been developed to access oxindole‐based sulfones through a 1,4‐cyano migration/cyclization process. Mechanistic studies indicate that the reaction proceeds through a radical pathway and confirm the intermediacy of aryl, sulfonyl, and iminyl radicals.

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Publication Details

Journal
Advanced Synthesis & Catalysis
Published
2026-08-13
DOI
https://doi.org/10.1002/adsc.70711
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
0.00
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article

Metal‐Free Synthesis of Oxindole‐Based Sulfones via 1,4‐Cyano Migration/Cyclization Through Radical SO 2 Insertion

Jie Wu, Wei Peng, Gang Liu, Wei Xiao et al.
Advanced Synthesis & Catalysis
Sulfur-Based Synthesis Techniques
article

Metal‐Free Synthesis of Oxindole‐Based Sulfones via 1,4‐Cyano Migration/Cyclization Through Radical SO 2 Insertion

Jie Wu, Wei Peng, Gang Liu, Wei Xiao, Jiaying Mi
article en

Abstract

Oxindole‐based sulfones are privileged structures found in bioactive compounds and natural products. Herein, a three‐component reaction of unactivated alkenes, potassium metabisulfite, and aryldiazonium tetrafluoroborates has been developed to access oxindole‐based sulfones through a 1,4‐cyano migration/cyclization process. Mechanistic studies indicate that the reaction proceeds through a radical pathway and confirm the intermediacy of aryl, sulfonyl, and iminyl radicals.

Advanced Synthesis & CatalysisVol. 368(16)
Chinese Academy of Sciences (CN), Jiangxi Science and Technology Normal University (CN), Shanghai Institute of Organic Chemistry (CN), Henan Normal University (CN), Taizhou University (CN)
Openalex Percentile: Top 18%
Sulfur-Based Synthesis Techniques
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