Issue 24, 2022

Remote C(sp3)–H heteroarylation of N-fluorocarboxamides with quinoxalin-2(1H)-ones under visible-light-induced photocatalyst-free conditions

Abstract

We report, for the first time, a visible-light-promoted remote benzylic/aliphatic C(sp3)–H heteroarylation of N-fluorocarboxamides with quinoxalin-2(1H)-ones. This transformation involves a sequence of amidyl radical generation, 1,5-hydrogen atom transfer (HAT), and cross-dehydrogenative coupling steps. By applying this new method, a broad range of biologically important 3-alkylated quinoxalin-2(1H)-ones (>60 examples) can be readily prepared at room temperature, thus showing the wide utility of this protocol. Notably, this practical reaction occurs under metal- and external photocatalyst-free conditions and exhibits a broad substrate scope, good functional group tolerance, and high chemoselectivity and regioselectivity.

Graphical abstract: Remote C(sp3)–H heteroarylation of N-fluorocarboxamides with quinoxalin-2(1H)-ones under visible-light-induced photocatalyst-free conditions

Supplementary files

Article information

Article type
Communication
Submitted
02 Aug. 2022
Accepted
30 Sept. 2022
First published
06 Okt. 2022

Green Chem., 2022,24, 9475-9481

Remote C(sp3)–H heteroarylation of N-fluorocarboxamides with quinoxalin-2(1H)-ones under visible-light-induced photocatalyst-free conditions

L. Xuan, R. Du, P. Lei, W. Zhao, L. Tan, C. Ni, H. Wang, Q. Yan, W. Wang and F. Chen, Green Chem., 2022, 24, 9475 DOI: 10.1039/D2GC02874C

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