What is "hydroacylation"

n. (context organic chemistry English) Any addition reaction in which an acyl group and a hydrogen atom (from an aldehyde) are added across a double bond

Hydroacylation is a type of organic reaction in which an aldehyde is added over an alkene or alkyne bond. The reaction product is a ketone. The reaction requires a metal catalyst, often rhodium. It is almost invariably practice as an intramolecular reaction. With an alkyne in place of alkenes, the reaction product is an α,β-unsaturated ketone.

The reaction was discovered as part of a synthetic route to certain prostanoids. The reaction required tin tetrachloride and a stoichiometric amount of Wilkinson's catalyst. An equal amount of a cyclopropane was formed as the result of decarbonylation.

The first catalytic application was reported by Miller in 1976. In their reaction, treatment of 4-pentenal with Wilkinson's catalyst gave cyclopentanone. In this reaction the solvent was saturated with ethylene.

Another suitable catalyst is the salt Rh( dppe)ClO.