Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 27, Issue 72, Pages 18168-18174Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202103486
Keywords
carboxylic acids; ketones; nickel; photocatalysis; radicals
Categories
Funding
- Projekt DEAL
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This method utilizes Hantzsch ester as a photoreductant and nickel catalyst to couple various radicals with aryl and alkyl acyl groups. The reaction proceeds under mild conditions without the need for toxic metal reagents or bases, showing wide applicability in pharmaceuticals and complex molecular architectures.
A simple visible light photochemical, nickel-catalyzed synthesis of ketones from carboxylic acid-derived precursors is presented. Hantzsch ester (HE) functions as a cheap, green and strong photoreductant to facilitate radical generation and also engages in the Ni-catalytic cycle to restore the reactive species. With this dual role, HE allows for the coupling of a large variety of radicals (1 degrees,2 degrees, benzylic, alpha-oxy & alpha-amino) with aroyl and alkanoyl moieties, a new feature in reactions of this type. With both precursors deriving from abundant carboxylic acids, this protocol is a welcome addition to the organic chemistry toolbox. The reaction proceeds under mild conditions without the need for toxic metal reagents or bases and shows a wide scope, including pharmaceuticals and complex molecular architectures.
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