Issue 34, 2017

Mild synthesis of triarylsulfonium salts with arynes

Abstract

Reactions between arynes and alkyl sulfides have been extensively studied over the past few decades. These reactions commonly end with a dealkylation process and thus deliver thioethers as final products. In contrast, the transformation described furnishes valuable triarylsulfonium salts, in lieu of thioethers, from arynes and diarylsulfides. The reaction features mild conditions and a broad substrate scope. A suite of functional groups such as ketones, esters, nitriles, aryl ethers and aryl halides is tolerated, which can be issues faced by traditional synthetic methods. The practicality of the reaction and its extension to the synthesis of triphenyl selenonium salt are also exhibited herein.

Graphical abstract: Mild synthesis of triarylsulfonium salts with arynes

Supplementary files

Article information

Article type
Paper
Submitted
01 Jul 2017
Accepted
08 Aug 2017
First published
08 Aug 2017

Org. Biomol. Chem., 2017,15, 7181-7189

Mild synthesis of triarylsulfonium salts with arynes

L. Zhang, X. Li, Y. Sun, W. Zhao, F. Luo, X. Huang, L. Lin, Y. Yang and B. Peng, Org. Biomol. Chem., 2017, 15, 7181 DOI: 10.1039/C7OB01596H

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