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January 22, 2026Synlett0 citations

K₂S₂O₈-KI Cooperative Oxidative System for Direct C3-Sulfenylation of Indoles with Thiols and Disulfides

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TBThewika BenchawanAJAmornrassamee JinnarakNSNakin Surapanich

Key Points

  • The aim is to develop a metal-free method for the direct C3-sulfenylation of indoles.
  • Utilized a KI/K₂S₂O₈ oxidative system
  • Conducted reactions in MeCN/H₂O at 60 °C
  • Tested various indole derivatives and sulfenylating agents
  • Achieved yields up to 93% for 3-sulfenylindoles
  • Successfully tolerated a range of electron-donating and electron-withdrawing substituents
  • Established a scalable and environmentally benign synthesis approach

Abstract

A mild and metal-free method for the direct C3-sulfenylation of indoles using a KI/K₂S₂O₈ oxidative system has been developed. The reaction proceeds efficiently in MeCN/H₂O at 60 °C, affording 3-sulfenylindoles in up to 93% yield without the need for transition metals or bases. A wide range of indole derivatives and aromatic sulfenylating agents bearing electron-donating or electron-withdrawing substituents are well tolerated. This protocol provides an efficient, scalable, and environmentally benign approach to the synthesis of 3-sulfenylindoles under simple operational conditions.

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Cite This Study

Benchawan et al. (2026) studied this question.

synapsesocial.com/papers/6971bd6a642b1836717e2155https://doi.org/10.1055/a-2788-6741
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