Intermolecular hydroalkylation of unactivated terminal alkenes with 1,3-diketones under neutral conditions has been achieved using a cationic iridium catalyst. An active C–H bond of 2,4-pentadione (2a) added to 1-octene (1a) under refluxing DCE to give a Markovnikov product in 88% yield. A broad scope of alkenes and 1,3-diketones was observed. The products were easily converted to heterocycles. This reaction provides a new method for extending a carbon chain from an unactivated aliphatic terminal alkene.

Transition-metal-catalyzed hydroalkylation of alkenes with 1,3-dicarbonyl compounds is a useful reaction to construct a C–C bond under neutral reaction conditions in a highly atom-economical manner. We found that hydroalkylation of aliphatic alkenes with β-ketoesters proceeded with the use of a cationic iridium complex and bidentate phosphine ligand to give selectively branched α-substituted β-ketoesters in high yields. The obtained hydroalkylated compounds can be converted to β-substituted ketones through one-pot Krapcho dealkoxycarbonylation.

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