HYDROGENATION OF ACETOPHENONE AND ITS DERIVATIVES WITH 2-PROPANOL USING AMINOMETHYLPHOSPHINE-RUTHENIUM CATALYSIS


KELEŞ M., Keles T., Serindag O., YAŞAR S., ÖZDEMİR İ.

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, vol.185, no.1, pp.165-170, 2010 (Peer-Reviewed Journal) identifier identifier

  • Publication Type: Article / Article
  • Volume: 185 Issue: 1
  • Publication Date: 2010
  • Doi Number: 10.1080/10426500902754278
  • Journal Name: PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
  • Journal Indexes: Science Citation Index Expanded, Scopus
  • Page Numbers: pp.165-170
  • Keywords: Acetophenone, aminomethylphosphine, hydrogenation, silica, ASYMMETRIC HYDROGENATION, AROMATIC KETONES, COMPLEXES, LIGANDS, SILICA, ALCOHOLS

Abstract

The reaction of 3'-aminopropyltriethoxysilane with the phosphonium salt ([Ph(2)P(CH(2)OH)(2)]Cl) gives an aminomethylphosphine-type ligand ((CH(3)CH(2)O)(3)Si(CH(2))(3)N(CH(2)PPh(2))(2)). Reaction of the ligand ((CH(3)CH(2)O)(3)Si(CH(2))(3)N(CH(2)PPh(2))(2)) with silica gives silica supported aminomethylphosphine ligand (SiO(2))-O-Si(CH(2))(3)N(CH(2)PPh(2))(2)). The ligands were refluxed with [RuCl(2)(p-cymene)](2) in toluene to give [RuCl(2)((CH(3)CH(2)O)(3)Si(CH(2))(3)N(CH(2)PPh(2))(2))] and silica-supported SiO(2))-O-[RuCl(2)((Si(CH(2))(3)N(CH(2)PPh(2))(2))(2)] complex, respectively. The catalytic studies show that the complexes [RuCl(2)((CH(3)CH(2)O)(3)Si(CH(2))(3)N(CH(2)PPh(2))(2))] and SiO(2))-O-[RuCl(2)((CH(3)CH(2)O)(3)Si(CH(2))(3)N(CH(2)PPh(2))(2))(2)] are very active catalysts for the transfer hydrogenation of acetophenone by 2-propanol in basic media. The best yield was observed in hydrogenation of m-methoxy acetophenone (95%) with catalyst [RuCl(2)((CH(3)CH(2)O)(3)Si(CH(2))(3)N(CH(2)PPh(2))(2))].