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August 16, 2026Advanced Synthesis & Catalysis

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

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Authors

WPWei PengJMJiaying MiGLGang Liu

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Overview

Synthetic study demonstrates metal-free generation of oxindole-based sulfones via three-component radical cyclization, highlighting a novel sulfur dioxide insertion pathway.

Key Points

  • To establish a metal-free, three-component synthetic protocol for accessing bioactive oxindole-based sulfones via radical sulfur dioxide insertion and 1,4-cyano migration.
  • Reacted unactivated alkenes with potassium metabisulfite (as the SO2 source) and aryldiazonium tetrafluoroborates in a three-component system.
  • Performed mechanistic studies to trace reaction intermediates and evaluate the pathway.
  • Successfully produced oxindole-based sulfones under metal-free conditions using a tandem 1,4-cyano migration and cyclization process.
  • Identified and confirmed key reactive intermediates, establishing a radical pathway driven by aryl, sulfonyl, and iminyl radicals.

Cite This Study

Peng et al. (2026) studied this question.

synapsesocial.com/papers/6a8179cbf2fb91fc834ad1a2https://doi.org/10.1002/adsc.70711
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Also Consider

Synapse has enriched 5 closely related papers on similar clinical questions. Consider them for comparative context:

  1. 1Construction of SulfonylOxindoles via a Radical-MediatedRelay Strategy of Sulfur Dioxide Insertion/Cyano Migration/Cyclization2026
  2. 2A Catalyst-Free Three-Component Approach to Sulfonated Indole-Fused Diazepinones via SO <sub>2</sub> Insertion2026
  3. 3Synthesis of FSO2-Functionalized Oxindoles via a Radical Fluorosulfonylation/Intramolecular Arylation Cascade2024
  4. 4Metal‐Free K<sub>2</sub>S<sub>2</sub>O<sub>8</sub> Mediated Synthesis of 3‐(Substituted)‐2‐Arylisoindolin‐1‐One Derivatives With Cascade C−N/C−C Bond Formations <i>Via</i> Radical Cyclization2024 · 4 citations
  5. 5Modular Assembly of Cyclic Sulfones via Radical Annulation with Unactivated Olefins2025