Issue 24, 2021

Site-specific C–H chalcogenation of quinoxalin-2(1H)-ones enabled by Selectfluor reagent

Abstract

A site-specific oxidative C–H chalcogenation of quinoxalin-2(1H)-ones with various diaryl diselenides/disulfides is presented by employing Selectfluor reagent as an oxidant. The reaction proceeds selectively at the C6 position of quinoxalin-2(1H)-ones, and enables access to a wide array of chalcogenyl quinoxalin-2(1H)-ones. The merits of the transformation involve excellent substrate and functional compatibility, operational simplicity, and the use of a mild oxidant. The present work offers a fundamental basis for the selective synthesis of functional quinoxalin-2(1H)-ones from readily available feedstocks.

Graphical abstract: Site-specific C–H chalcogenation of quinoxalin-2(1H)-ones enabled by Selectfluor reagent

Supplementary files

Article information

Article type
Research Article
Submitted
07 Sep 2021
Accepted
29 Oct 2021
First published
30 Oct 2021

Org. Chem. Front., 2021,8, 6937-6949

Site-specific C–H chalcogenation of quinoxalin-2(1H)-ones enabled by Selectfluor reagent

J. Yuan, Y. Zhang, G. Huang, M. Ma, T. Yang, L. Yang, S. Zhang, P. Mao and L. Qu, Org. Chem. Front., 2021, 8, 6937 DOI: 10.1039/D1QO01332G

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