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August 9, 2026The Journal of Organic Chemistry

Construction of SulfonylOxindoles via a Radical-MediatedRelay Strategy of Sulfur Dioxide Insertion/Cyano Migration/Cyclization

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Authors

ALAo-Yun LiHunan Institute of Science and TechnologyPHPeng‐Fei HuangHunan Institute of Science and TechnologyLZLong‐Jin ZhongHunan Institute of Science and Technology

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Overview

Randomized trial reveals a novel method for creating β-cyanosulfone-containing oxindoles, suggesting enhancements in synthetic chemistry.

Key Points

  • The aim is to develop a simple and efficient method for constructing β-cyanosulfone-containing oxindoles.
  • Established a three-component sulfonylation/cyanation process.
  • Utilized sulfur dioxide insertion combined with cyano migration and cyclization.
  • Executed the reaction under mild conditions without metals or photocatalysts.
  • Successfully synthesized β-cyanosulfone-containing oxindoles from unactivated alkenes.
  • Achieved the reaction via in situ formation of radical intermediates.
  • Avoided the use of unstable sulfonyl chlorides in the process.

Cite This Study

Li et al. (2026) studied this question.

synapsesocial.com/papers/6a782d4e2e1896536c840442https://doi.org/10.1021/acs.joc.6c01589
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Also Consider

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  1. 1Metal‐Free Synthesis of Oxindole‐Based Sulfones via 1,4‐Cyano Migration/Cyclization Through Radical SO <sub>2</sub> Insertion2026
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  3. 3Regioselective C2-Sulfonylation of Indoles and Pyrroles via SO <sub>2</sub> Insertions2026
  4. 4Photoredox Ring Opening 1,2-Alkylarylation of Alkenes with Sulfonium Salts Toward Thioether-Substituted Oxindoles2024 · 16 citations
  5. 5Photoinduced Multicomponent Sulfonylsulfination of Alkenes via Aromatization-Driven Deconstructive and Radical-Polar Crossover Cyclization Strategies2025