Upgrading ketone synthesis direct from carboxylic acids and organohalides

Rehanguli Ruzi, Kai Liu, Chengjian Zhu and Jin Xie ()
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Rehanguli Ruzi: Nanjing University
Kai Liu: Nanjing University
Chengjian Zhu: Nanjing University
Jin Xie: Nanjing University

Nature Communications, 2020, vol. 11, issue 1, 1-9

Abstract: Abstract The ketone functional group has a unique reactivity in organic chemistry and is associated with a number of useful reactions. Catalytic methods for ketone synthesis are continually being developed. Here, we report a photoredox, nickel and phosphoranyl radical synergistic cross-electrophile coupling of commercially available chemicals, aromatic acids and aryl/alkyl bromides. This allows for concise synthesis of highly functionalized ketones directly, without the preparation of activated carbonyl intermediates or organometallic compounds, and thus complements the conventional Weinreb ketone synthesis. Use of the appropriate photocatalyst, ligand amount and solvents can match the reaction rate required by any simple catalytic cycle. The practicality and synthetic robustness of the reaction are illustrated by the facile synthesis of complex ketones from readily available feedstock chemicals.

Date: 2020
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DOI: 10.1038/s41467-020-17224-2

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