Issue 2, 2023

Visible-light-photocatalysis driven denitrogenative/radical 1,3-shift of benzotriazole: access to 3-aryl-aminoquinoxalin-2(1H)-one scaffolds

Abstract

The visible-light-photocatalysis driven denitrogenative/radical 1,3-shift of benzotriazole to generate an unusual aromatic amine radical and then construct diverse 3-aryl-aminoquinoxalin-2(1H)-ones bearing great synthetic values is disclosed. This photocatalytic reaction allows the direct formation of 3-aryl-aminoquinoxalin-2(1H)-ones with highly tolerant functional groups. Furthermore, preliminary mechanistic investigations indicated that the reaction was induced by visible light and underwent the radical pathway. Insights gained from our studies are expected to advance general efforts to provide a green, economical and concise strategy to access 3-aryl-aminoquinoxalin-2(1H)-ones, and also offer new opportunities towards obtaining arylamine radical and aromatic amine sources.

Graphical abstract: Visible-light-photocatalysis driven denitrogenative/radical 1,3-shift of benzotriazole: access to 3-aryl-aminoquinoxalin-2(1H)-one scaffolds

Supplementary files

Article information

Article type
Research Article
Submitted
18 Oct 2022
Accepted
06 Dec 2022
First published
07 Dec 2022

Org. Chem. Front., 2023,10, 531-539

Visible-light-photocatalysis driven denitrogenative/radical 1,3-shift of benzotriazole: access to 3-aryl-aminoquinoxalin-2(1H)-one scaffolds

B. Yi, H. Tang, Z. Yi, H. Gong, D. Li, W. Zhang, Y. Chen, J. Tan and Y. Xie, Org. Chem. Front., 2023, 10, 531 DOI: 10.1039/D2QO01635D

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