Issue 44, 2018

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

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

Supplementary files

Article information

Article type
Communication
Submitted
25 Mar 2018
Accepted
01 May 2018
First published
02 May 2018

Chem. Commun., 2018,54, 5574-5577

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements