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Upgrading ketone synthesis direct from carboxylic acids and organohalides.

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.

SUBMITTER: Ruzi R

PROVIDER: S-EPMC7334210 | biostudies-literature | 2020 Jul

REPOSITORIES: biostudies-literature

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Upgrading ketone synthesis direct from carboxylic acids and organohalides.

Ruzi Rehanguli R Liu Kai K Zhu Chengjian C Xie Jin J

Nature communications 20200703 1

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 ...[more]

PMID: 32620758

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