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Issue 44, 2018
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Copper-catalyzed selective radical–radical cross-coupling for C–S bond formation: an access to α-alkylthionitriles

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Abstract

A new protocol for C–S bond formation was developed by selective cross-coupling between a thiyl radical and an isobutyronitrile radical. Using this strategy, a series of valuable α-alkylthionitrile derivatives were synthesized from basic starting materials. Preliminary mechanistic investigation was performed by EPR and XAFS, revealing that the transient thiyl radical could be stabilized by a copper catalyst to a persistent one. Therefore, on the basis of the persistent radical effect, selective radical–radical cross-coupling between the thiyl radical and the isobutyronitrile radical was achieved successfully in this work.

Graphical abstract: Copper-catalyzed selective radical–radical cross-coupling for C–S bond formation: an access to α-alkylthionitriles

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Publication details

The article was received on 25 Mar 2018, accepted on 01 May 2018 and first published on 02 May 2018


Article type: Communication
DOI: 10.1039/C8CC02371A
Citation: Chem. Commun., 2018,54, 5574-5577
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    Copper-catalyzed selective radical–radical cross-coupling for C–S bond formation: an access to α-alkylthionitriles

    C. Zheng, F. Lu, H. Lu, J. Xin, Y. Deng, D. Yang, S. Wang, Z. Huang, M. Gao and A. Lei, Chem. Commun., 2018, 54, 5574
    DOI: 10.1039/C8CC02371A

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