Tunable ferrocenyl-phosphinite ligands for the ruthenium(II)-catalyzed asymmetric transfer hydrogenation of ketones

Isik U., Aydemir M., Meric N., Durap F., Kayan C., Temel H., ...More

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, vol.379, pp.225-233, 2013 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 379
  • Publication Date: 2013
  • Doi Number: 10.1016/j.molcata.2013.08.005
  • Journal Name: JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.225-233
  • Keywords: Monodendate ferrocenyl-phosphinite, Homogeneous catalysis, Asymmetric transfer hydrogenation, Aromatic ketones, Ruthenium(II), CATALYZED ENANTIOSELECTIVE HYDROGENATION, RAY CRYSTAL-STRUCTURE, AROMATIC KETONES, CHIRAL LIGANDS, C-2-SYMMETRIC AXIS, PHOSPHORUS LIGANDS, METAL-COMPLEXES, ALCOHOLS, RH, BIS(PHOSPHINITE)
  • Yozgat Bozok University Affiliated: No

Abstract

We report here new examples of enantiomerically pure monodendate phosphinite ligands containing both a ferrocene moiety and NH bridging moiety adjacent to the stereocenter, as well as their ruthenium(II) dichloro complexes. The phosphinites based on ferrocenyl moiety possessing stereogenic center have been screened as ligands for ruthenium(II)-catalyzed transfer hydrogenation of aromatic ketones to give corresponding secondary alcohols using iso-PrOH as the hydrogen source in the presence of NaOH. Up to 99% conversion with 97% ee was obtained in the transfer hydrogenation of acetophenone derivatives. Furthermore, the catalytic properties of these catalysts based on ferrocenyl-phosphinite backbone are also discussed briefly. The structures of these ligand and their corresponding complexes have been elucidated by a combination of multinuclear NMR spectroscopy, IR spectroscopy and elemental analysis. (C) 2013 Elsevier B.V. All rights reserved.