Phosphine-Mediated Decarboxylative C(sp3)–S Cross-Coupling of Aliphatic Carboxylic Acids Using Diaryl Disulfides as Bifunctional Reagents

Abstract Herein, we report a phosphine-mediated decarboxylative thioetherification of aliphatic carboxylic acids. This method uses odorless diaryl disulfides as bifunctional reagents, activating aliphatic carboxylic acid substrates and providing a sulfur source. This strategy features mild conditions, is free of transition metals and photocatalysts, tolerates diverse functional groups, and enables the late-stage modification of bioactive molecules. Furthermore, mechanistic studies support a radical pathway involving thioester and NHPI ester intermediates.

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Publication Details

Journal
Organic Letters
Published
2026-09-25
DOI
https://doi.org/10.1021/acs.orglett.6c03122
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
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article

Phosphine-Mediated Decarboxylative C(sp3)–S Cross-Coupling of Aliphatic Carboxylic Acids Using Diaryl Disulfides as Bifunctional Reagents

Lan Yang, Penglin Zhang, Siyu Gao, Xiao-Hui Ye
Organic Letters
Sulfur-Based Synthesis Techniques
article

Phosphine-Mediated Decarboxylative C(sp3)–S Cross-Coupling of Aliphatic Carboxylic Acids Using Diaryl Disulfides as Bifunctional Reagents

Lan Yang, Penglin Zhang, Siyu Gao, Xiao-Hui Ye
article en

Abstract

Abstract Herein, we report a phosphine-mediated decarboxylative thioetherification of aliphatic carboxylic acids. This method uses odorless diaryl disulfides as bifunctional reagents, activating aliphatic carboxylic acid substrates and providing a sulfur source. This strategy features mild conditions, is free of transition metals and photocatalysts, tolerates diverse functional groups, and enables the late-stage modification of bioactive molecules. Furthermore, mechanistic studies support a radical pathway involving thioester and NHPI ester intermediates.

Organic Letters
Tianjin University of Science and Technology (CN)
Clean water and sanitation
Openalex Percentile: Top 22%
Sulfur-Based Synthesis Techniques
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Phosphine-Mediated Decarboxylative C(sp3)–S Cross-Coupling of Aliphatic Carboxylic Acids Using Diaryl Disulfides as Bifunctional Reagents — Lan Yang, Penglin Zhang, et al. · Organic Letters (2026) | TGRS Research Map | TGRS