Premium
Nickel‐Mediated Photoreductive Cross Coupling of Carboxylic Acid Derivatives for Ketone Synthesis **
Author(s) -
Brauer Jan,
Quraishi Elisabeth,
Kammer Lisa Marie,
Opatz Till
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202103486
Subject(s) - chemistry , ketone , catalysis , radical , reagent , nickel , carboxylic acid , combinatorial chemistry , organic synthesis , catalytic cycle , organic chemistry
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°,2°, benzylic, α‐oxy & α‐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.