Metal-Free Addition of Alkyl Bromides to Access 3,3-Disubstituted Quinoxalinones Enabled by Visible-Light Photoredox Catalysis

Metal-Free Addition of Alkyl Bromides to Access 3,3-Disubstituted Quinoxalinones Enabled by Visible-Light Photoredox Catalysis

A metal-free addition of unactivated alkyl bromides to quinoxalin-2­(1H)-ones is described. This method enables the construction of valuable 3,3-disubstituted dihydroquinoxalin-2­(1H)-ones bearing quaternary carbon centers under mild, visible-light photoredox catalysis. High functional group toleran...

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Veröffentlicht in:Journal of organic chemistry 2023-08, Vol.88 (16), p.11762-11766
Hauptverfasser: Liao, Jennie, Hunter, David N., Oloyede, Ugochinyere Nancy, McLaughlin, Joseph W., Wang, Cheng, El Marrouni, Abdellatif
Format: Artikel
Sprache:eng
Schlagworte:
carbon
catalytic activity
light
organic chemistry
redox reactions
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Zusammenfassung:A metal-free addition of unactivated alkyl bromides to quinoxalin-2­(1H)-ones is described. This method enables the construction of valuable 3,3-disubstituted dihydroquinoxalin-2­(1H)-ones bearing quaternary carbon centers under mild, visible-light photoredox catalysis. High functional group tolerance is observed in both the quinoxalinone and alkyl bromide partners. The ability to scale up this method was demonstrated under photo-flow conditions to enable gram-scale synthesis.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.3c01054