Asymmetric Hydrogenation of Acetophenone Catalyzed by Chirally Modified Ruthenium Nanoparticles Supported on Carbon Nanotubes

Abstract

AbstractDifferent types of carbon nanotubes as carriers were used to prepare ruthenium nano‐catalysts loaded outside (named as Ru/CNTs) and inside (named as Ru@CNTs) the tube. The catalysts were modified in situ with chiral ligands (1S, 2S)‐DPEN (1S, 2S)‐DPEN=(1S, 2S)‐1,2‐diphenyl‐1,2‐ethanediamine). In the presence of TPP (TPP=triphenylphosphine) as the stabilization, the catalytic asymmetric hydrogenation of acetophenone was carried out with the modified catalysts. A novel approach to prepare the inside‐loaded catalysts of Ru@CNTs was explored in the preparation. The catalyst can efficiently prevent the Ru nanoparticles from oxidizing in the air in this approach. The catalysts were well characterized by means of TEM, XRD, XPS, BET and H2 Pulse Chemisorption. The effect of the diameter of carbon nanotubes on the particle size of ruthenium nanoparticles loaded on the tubes was also well studied. When Ru@CNTs (8 %, S) (“S” abbreviated from “short”, the same below) was used in the asymmetric hydrogenation of acetophenone, 100 % conversion of acetophenone achieved, and the ee value reached 76.4 %. Under the same reaction conditions, 100 % conversion of acetophenone as well as the highest ee value of 80.8 % were obtained when Ru/CNTs (8 %, S) was applied in the reaction.