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A redox-neutral synthesis of ketones by coupling of alkenes and amides.

ABSTRACT: The direct synthesis of ketones via carbon-carbon bond formation represents one of the most important challenges in organic synthesis. Hydroacylation of alkenes offers perhaps the most efficient and atom-economical approach for the preparation of ketones employing carbonyl compounds and alkenes as feedstocks. State-of-the-art hydroacylation is typically achieved by a transition metal-catalysed coupling of an aldehyde and an alkene but is plagued by competing decarbonylation, requiring the installation of directing groups in the aldehyde reactant. Herein, we present a method for the hydroacylation of alkenes employing amides in a metal-free regime, proceeding by a new mechanism and offering orthogonal reactivity to the conventional, metal-catalysed alternatives.

SUBMITTER: Li J

PROVIDER: S-EPMC6534616 | biostudies-literature | 2019 May

REPOSITORIES: biostudies-literature

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A redox-neutral synthesis of ketones by coupling of alkenes and amides.

Li Jing J Oost Rik R Maryasin Boris B González Leticia L Maulide Nuno N

Nature communications 20190524 1

The direct synthesis of ketones via carbon-carbon bond formation represents one of the most important challenges in organic synthesis. Hydroacylation of alkenes offers perhaps the most efficient and atom-economical approach for the preparation of ketones employing carbonyl compounds and alkenes as feedstocks. State-of-the-art hydroacylation is typically achieved by a transition metal-catalysed coupling of an aldehyde and an alkene but is plagued by competing decarbonylation, requiring the instal ...[more]

PMID: 31127092

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