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

Jing Li, Rik Oost, Boris Maryasin, Leticia González and Nuno Maulide ()
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Jing Li: University of Vienna
Rik Oost: University of Vienna
Boris Maryasin: University of Vienna
Leticia González: University of Vienna
Nuno Maulide: University of Vienna

Nature Communications, 2019, vol. 10, issue 1, 1-7

Abstract: 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.

Date: 2019
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DOI: 10.1038/s41467-019-10151-x

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