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Elemental sulfur as a sulfuration agent in the copper-catalyzed C–H bond thiolation of electron-deficient arenes

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Abstract

By utilizing elemental sulfur as the thiolation agent and oxidant, a copper-catalyzed direct C–H bond thiolation of electron-deficient arenes was demonstrated. Various electron-deficient arenes were proved to be suitable for this transformation. Preliminary mechanistic studies indicated that this reaction underwent a radical pathway, in which the trisulfur radical anion (S3˙) might play a vital role. Meanwhile, KIE experiments suggested that C–H bond cleavage was not involved in the rate-determining step.

Graphical abstract: Elemental sulfur as a sulfuration agent in the copper-catalyzed C–H bond thiolation of electron-deficient arenes

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Publication details

The article was received on 16 Aug 2017, accepted on 12 Sep 2017 and first published on 13 Sep 2017


Article type: Communication
DOI: 10.1039/C7OB02036H
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Elemental sulfur as a sulfuration agent in the copper-catalyzed C–H bond thiolation of electron-deficient arenes

    H. Yan, Z. Huang, M. Chen, C. Li, Y. Chen, M. Gao and A. Lei, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB02036H

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