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2000
Volume 22, Issue 4
  • ISSN: 1570-1794
  • E-ISSN: 1875-6271

Abstract

Background

An efficient method for synthesizing cyclic arylsulfonium salts has been developed by selective aryl transfer to the sulfur atom from aryl(mesityl)iodonium triflates, a recyclable series of diaryliodonium salts.

Methods

The utilization of sulfonium salts as valuable intermediates is well-established, as they exhibit high reactivity under conditions of heating or UV irradiation. However, their synthesis typically involves the reaction of diarysulfoxide with acid anhydride, which requires the oxidation of sulfur(II) to sulfoxide(IV) and thus limits the scope of synthesis. Hence, in this study, we employed recyclable mesityliodonium(III) salts and copper catalysis.

Results

The method was used to synthesize cyclic arylsulfonium salts without the need for pre-oxidation of the sulfur atom, resulting in a facile and high-yield synthesis.

Conclusion

The desired cyclic arylsulfonium salts were synthesized through selective transfer of the aryl group from mesityliodonium salts, demonstrating the effectiveness of the new approach.

© 2025 Bentham Science Publishers
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2024-07-22
2025-09-02

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Synthesis of Heterocyclic Sulfonium Triflates by Cu-catalyzed Selective S-arylation with Aryl(mesityl)iodonium Salts
Curr. Org. Synth. 22, 531 (2025); https://doi.org/10.2174/0115701794298369240607042545
/content/journals/cos/10.2174/0115701794298369240607042545
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Supplements

Supportive/Supplementary material will be available on the journal’s website. 1H, 19F, 13C spectra charts of the sulfonium salt products are available as supplementary material.

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  • Article Type:     Research Article
Keyword(s): aryl transfer; heterocyclic sulfur compounds; Hypervalent iodine; mesityliodonium salts; S-arylation; sulfonium salts

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