Hydrogenation of aromatic ketones catalyzed by (η5-C5(CH3)5)Ru complexes bearing primary amines

The rapid hydrogenation of simple aromatic ketones is accomplished by using a combination of (eta (5)- C-5(CH3)(5)) Ru complexes and primary amines as a catalyst in 2-propanol. In particular, 1,2-diamines with primary and tertiary amino groups at both ends exhibit a significant ligand acceleration effect. Isotope-labeling experiments using D-2 and 2-propanol-d(n) reveal that 2-propanol participates in the activation of H-2 based on a metal/NH bifunctional effect to facilitate the hydrogenation. Asymmetric hydrogenation of prochiral simple ketones with the chiral version of the catalysts provides optically active secondary alcohols with rip to 95% ee.