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.