Novel cyclohexyl-based aminophosphine ligands and use of their Ru(II) complexes in transfer hydrogenation of ketones

Kayan C., Meric N., Aydemir M., Ocak Y. S., Baysal A., Temel H.

APPLIED ORGANOMETALLIC CHEMISTRY, vol.28, no.2, pp.127-133, 2014 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 28 Issue: 2
  • Publication Date: 2014
  • Doi Number: 10.1002/aoc.3096
  • Journal Name: APPLIED ORGANOMETALLIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.127-133
  • Keywords: aminophosphine, ruthenium(II), transfer hydrogenation, homogeneous catalysis, ASYMMETRIC TRANSFER HYDROGENATION, ENANTIOSELECTIVE TRANSFER HYDROGENATION, CATALYZED TRANSFER HYDROGENATION, TRANSITION-METAL-COMPLEXES, X-RAY-STRUCTURE, AROMATIC KETONES, C-H, STEREOSELECTIVE HYDROGENATION, ORGANOMETALLIC CHEMISTRY, RUTHENIUM(II) COMPLEXES
  • Yozgat Bozok University Affiliated: No

Abstract

Two new aminophosphines - furfuryl-(N-dicyclohexylphosphino)amine, [Cy2PNHCH2-C4H3O] (1) and thiophene-(N-dicyclohexylphosphino)amine, [Cy2PNHCH2-C4H3S] (2) - were prepared by the reaction of chlorodicyclohexylphosphine with furfurylamine and thiophene-2-methylamine. Reaction of the aminophosphines with [Ru((6)-p-cymene)(-Cl)Cl](2) or [Ru((6)-benzene)(-Cl)Cl](2) gave corresponding complexes [Ru(Cy2PNHCH2-C4H3O)((6)-p-cymene)Cl-2] (1a), [Ru(Cy2PNHCH2-C4H3O)((6)-benzene)Cl-2] (1b), [Ru(Cy2PNHCH2-C4H3S)((6)-p-cymene)Cl-2] (2a) and [Ru(Cy2PNHCH2-C4H3S)((6)-benzene)Cl-2] (2b), respectively, which are suitable catalyst precursors for the transfer hydrogenation of ketones. In particular, [Ru(Cy2PNHCH2-C4H3S)((6)-benzene)Cl-2] acts as a good catalyst, giving the corresponding alcohols in 98-99% yield in 30min at 82 degrees C (up to time of flight588h(-1)). Copyright (c) 2014 John Wiley & Sons, Ltd.