Journal
GREEN CHEMISTRY
Volume 24, Issue 24, Pages -Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2gc02874c
Keywords
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Funding
- National Natural Science Foundation of China [21602144]
- Scientific Research Project of the Education Department of Hubei Province [Q20211503]
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A visible-light-promoted remote benzylic/aliphatic C(sp(3))-H heteroarylation of N-fluorocarboxamides with quinoxalin-2(1H)-ones is reported for the first time. This transformation allows the synthesis of a wide range of biologically important 3-alkylated quinoxalin-2(1H)-ones under metal- and external photocatalyst-free conditions. The method shows good substrate scope, functional group tolerance, chemoselectivity, and regioselectivity.
We report, for the first time, a visible-light-promoted remote benzylic/aliphatic C(sp(3))-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.
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