Ruthenium-Catalyzed Cross-Coupling of Ketones as an Alkenyl Electrophile with Organoborons via Cleavage of Alkenyl C–N Bonds of in Situ Generated Enamines

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.