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Chinese Journal of Organic Chemistry >

0 8022

DOI: https://doi.org/10.6023/cjoc202508022

ARTICLE

Electrochemical Synthesis of 4-Sulfenylisocoumarins via Radical Cascade Annulation of o-Alkynylbenzoates with Thiophenols

  • Chao Ma ,
  • Xiaoling Xu ,
  • Xiang Luo ,
  • Ruijuan Lu ,
  • Guoqi Yu ,
  • Tao Cai
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  • aCollege of Chemistry and Chemical Engineering, Shaoxing University, Shaoxing, 312000;
    bZhejiang Engineering Research Center of Fat-Soluble Vitamin, Shaoxing University, Shaoxing, 312000

Received date: 2025-08-25

  Revised date: 2025-10-15

  Online published: 2025-11-27

Supported by

Shaoxing Basic Public Welfare Project (No. 2023A11003), and the Research Project of Shaoxing University (No. 2023LG003)

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Abstract

This study presents the first electrochemical method that employs commercially available, stable, and inexpensive thiophenols as sulfenylating agents for the efficient synthesis of valuable 4-sulfenylisocoumarins. Various thiophenols containing both electron-donating and electron-withdrawing groups reacted smoothly with o-alkynylbenzoates to afford the corresponding 4-sulfenylisocoumarins in moderate to good yields. Preliminary mechanistic investigation, including controlled experiments and cyclic voltammetry (CV) experiments, indicated that this electrochemical cyclization might proceed via a radical pathway. In comparison to existing methods, this strategy circumvents the need for moisture-sensitive and pre-functionalized sulfenylating reagents, significantly broadens the substrate scope, and offers a practical and sustainable alternative for the synthesis of 4-sulfenylisocoumarins.

Key words： 4-Sulfenylisocoumarins; thiophenol; o-alkynylbenzoates; electrochemical synthesis; radical cascade annulation

Cite this article

Chao Ma , Xiaoling Xu , Xiang Luo , Ruijuan Lu , Guoqi Yu , Tao Cai . Electrochemical Synthesis of 4-Sulfenylisocoumarins via Radical Cascade Annulation of o-Alkynylbenzoates with Thiophenols[J]. Chinese Journal of Organic Chemistry, 0 : 8022 . DOI: 10.6023/cjoc202508022

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