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Issue 34, 2017
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Mild synthesis of triarylsulfonium salts with arynes

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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

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The article was received on 01 Jul 2017, accepted on 08 Aug 2017 and first published on 08 Aug 2017

Article type: Paper
DOI: 10.1039/C7OB01596H
Citation: Org. Biomol. Chem., 2017,15, 7181-7189
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    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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