A redox-neutral synthesis of ketones by coupling of alkenes and amides.
basic_science · Level V
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- Record sourced from PubMed, PMID 31127092.
- Also identified by DOI 10.1038/s41467-019-10151-x and PMC identifier 6534616.
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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.