Issue 23, 2022
From the journal:

Organic Chemistry Frontiers

Catalyst-free aerobic radical cascade reactions of o-vinylphenylisocyanides with thiols to access 2-thio-substituted quinolines†

Jin Wang,‡*a   Haitao Liu,‡a   Yaohui Liu,a   Wanting Hao,a   Yingqi Yang,a   Yanan Suna  and  Xianxiu Xu ORCID logo *a  

* Corresponding authors

a College of Chemistry, Chemical Engineering and Materials Science, Key Laboratory of Molecular and Nano Probes, Ministry of Education, Shandong Normal University, Jinan 250014, China
E-mail: jinwang@sdnu.edu.cn, xuxx677@sdnu.edu.cn

Abstract

We herein report an efficient and green aerobic radical cascade reaction of o-vinylphenylisocyanides with thiols to access a broad range of 2-thio-substituted quinolines without the need for additional catalysts or oxidants. Mechanistic investigations suggested that this reaction was initiated by a thiyl radical generated under aerobic conditions to form thioimidoyl radicals, followed by radical annulation with a vinyl substituent.

Graphical abstract: Catalyst-free aerobic radical cascade reactions of o-vinylphenylisocyanides with thiols to access 2-thio-substituted quinolines

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Article information

DOI
https://doi.org/10.1039/D2QO01371A
Article type
Research Article
Submitted
29 Aug 2022
Accepted
05 Oct 2022
First published
07 Oct 2022

Org. Chem. Front., 2022,9, 6484-6489

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Catalyst-free aerobic radical cascade reactions of o-vinylphenylisocyanides with thiols to access 2-thio-substituted quinolines

J. Wang, H. Liu, Y. Liu, W. Hao, Y. Yang, Y. Sun and X. Xu, Org. Chem. Front., 2022, 9, 6484 DOI: 10.1039/D2QO01371A

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