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Synthesis of unsymmetrical disulfides via PPh3-mediated reductive coupling of thiophenols with sulfonyl chlorides

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Abstract

A facile and rapid synthesis of unsymmetrical aryl disulfides using PPh3-mediated reductive coupling of thiophenols with aryl sulfonyl chlorides was described. Good functional group tolerance and scalability were achieved in this strategy. More importantly, the approach enables the introduction of sulfonyl chlorides into the synthesis of asymmetric organic disulfides under catalyst- and base-free conditions. Using this method, unsymmetrical aromatic disulfides could be prepared from inexpensive and readily available starting materials in moderate to excellent isolated yields, through a nucleophilic substitution pathway.

Graphical abstract: Synthesis of unsymmetrical disulfides via PPh3-mediated reductive coupling of thiophenols with sulfonyl chlorides

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Supplementary files

Article information


Submitted
18 Apr 2020
Accepted
20 May 2020
First published
21 May 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Paper

Synthesis of unsymmetrical disulfides via PPh3-mediated reductive coupling of thiophenols with sulfonyl chlorides

D. Wang, X. Liang, M. Xiong, H. Zhu, Y. Zhou and Y. Pan, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/D0OB00804D

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