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Issue 18, 2020

Visible-light induced phosphonation of quinoxalines and quinoxalin-2(1H)-ones under aerobic metal-free conditions

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Abstract

Phosphonation of quinoxalines and quinoxalin-2(1H)-ones utilizing aerobic oxygen as green oxidant under visible light conditions at room temperature has been described. Both quinoxalines and quinoxalin-2(1H)-ones are compatible with alkyl or aryl phosphonates and provided good yields of products through regioselective C–P bond formation under base/ligand-free conditions. Competitive experiments showed quinoxalin-2(1H)-ones are more reactive than quinoxalines under the present conditions, and the control experiments revealed the present transformation proceeds through a radical mechanism.

Graphical abstract: Visible-light induced phosphonation of quinoxalines and quinoxalin-2(1H)-ones under aerobic metal-free conditions

Supplementary files

Article information


Submitted
25 Jun 2020
Accepted
28 Aug 2020
First published
28 Aug 2020

Green Chem., 2020,22, 6170-6175
Article type
Paper

Visible-light induced phosphonation of quinoxalines and quinoxalin-2(1H)-ones under aerobic metal-free conditions

D. Rawat, R. Kumar and A. Subbarayappa, Green Chem., 2020, 22, 6170 DOI: 10.1039/D0GC02168G

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