Ruthenium-Catalyzed Cross-Coupling of Ketones as an Alkenyl Electrophile with Organoborons via Cleavage of Alkenyl C–N Bonds of in Situ Generated Enamines
Yuya Kogure, Satoshi Ueno
Abstract
A ruthenium-catalyzed cross-coupling reaction of ketones with organoboronic esters was developed. In this reaction, ketones possessing a pyridine-directing group directly functions as an alkenyl electrophile for coupling with organoboronates in the presence of pyrrolidine and a ruthenium catalyst. This reaction proceeds via the catalytic cleavage of the alkenyl carbon-nitrogen bond in the enamines generated in situ from ketones with pyrrolidine, benzylamine, or isoindoline.
Topics & Concepts
ChemistryElectrophileRutheniumCatalysisIn situCleavage (geology)Bond cleavageCoupling (piping)Medicinal chemistryStereochemistryOrganic chemistryFracture (geology)Mechanical engineeringGeotechnical engineeringEngineeringCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsAsymmetric Hydrogenation and Catalysis