Iridium-Catalyzed Hydroalkylation of Aliphatic Alkenes with β-Ketoesters: Formal Hydroalkylation with Methyl Ketones
Takahiro Sawano, Kei Ogihara, Jun Sagawa, Masaki Ono, Ryo Takeuchi
Abstract
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.
Topics & Concepts
ChemistryCatalysisIridiumOrganic chemistryFormal synthesisCombinatorial chemistryMedicinal chemistryAsymmetric Hydrogenation and CatalysisCatalytic C–H Functionalization MethodsOrganometallic Complex Synthesis and Catalysis