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

Org Biomol Chem

Key Laboratory of Biocatalysis & Chiral Drug Synthesis of Guizhou Province, Generic Drug Research Center of Guizhou Province, Department of Pharmacy, Zunyi Medical University, 6 Xuefu Road West, Zunyi, 563000, China.

Published: March 2021

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.

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http://dx.doi.org/10.1039/d0ob02364gDOI Listing

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