Issue 9, 2021

Catalyst-free generation of acyl radicals induced by visible light in water to construct C–N bonds

Abstract

We describe herein a catalyst-free and redox-neutral photochemical strategy for the direct generation of acyl radicals from α-diketones, and its selective conversion of nitrosoarenes to hydroxyamides or amides with AcOH or NaCl as an additive. The reaction was carried out under mild conditions in water with purple LEDs as the light source. A broad scope of substrates was demonstrated. Mechanistic experiments indicate that α-diketones cleave to give acyl radicals, with hydroxyamides being further reduced to amides.

Graphical abstract: Catalyst-free generation of acyl radicals induced by visible light in water to construct C–N bonds

Supplementary files

Article information

Article type
Paper
Submitted
27 Nov 2020
Accepted
04 Jan 2021
First published
05 Jan 2021

Org. Biomol. Chem., 2021,19, 1970-1975

Catalyst-free generation of acyl radicals induced by visible light in water to construct C–N bonds

M. Ran, J. He, B. Yan, W. Liu, Y. Li, Y. Fu, C. Li and Q. Yao, Org. Biomol. Chem., 2021, 19, 1970 DOI: 10.1039/D0OB02364G

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