Issue 14, 2022
From the journal:

Organic Chemistry Frontiers

Copper-catalyzed regioselective 1,4-sulfonylcyanation of 1,3-enynes with sulfonyl chlorides and TMSCN†

Yunhe Lv, ORCID logo *a   Wanru Han,a   Weiya Pu,a   Jinhui Xie,a   Axue Wang,a   Mengyue Zhang,a   Jin Wanga  and  Junrong Laia  

* Corresponding authors

a College of Chemistry and Chemical Engineering, Anyang Normal University, Anyang, P. R. China
E-mail: luyh086@nenu.edu.cn, lvyunhe0217@163.com

Abstract

A novel and practical copper-catalyzed reaction for the 1,4-sulfonylcyanation of 1,3-enynes under mild conditions is described. This protocol provides efficient and straightforward access to a variety of 5-sulfonylpenta-2,3-dienenitrile derivatives with excellent functional group tolerance and good regioselectivity from readily available 1,3-enynes and commercially available sulfonyl chlorides and TMSCN. A mechanism involving sulfonyl and allenyl radical species is proposed.

Graphical abstract: Copper-catalyzed regioselective 1,4-sulfonylcyanation of 1,3-enynes with sulfonyl chlorides and TMSCN

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Article information

DOI
https://doi.org/10.1039/D2QO00486K
Article type
Research Article
Submitted
26 Mar 2022
Accepted
02 Jun 2022
First published
06 Jun 2022

Org. Chem. Front., 2022,9, 3775-3780

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Copper-catalyzed regioselective 1,4-sulfonylcyanation of 1,3-enynes with sulfonyl chlorides and TMSCN

Y. Lv, W. Han, W. Pu, J. Xie, A. Wang, M. Zhang, J. Wang and J. Lai, Org. Chem. Front., 2022, 9, 3775 DOI: 10.1039/D2QO00486K

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