586985-91-3Relevant academic research and scientific papers
A modular design of metal catalysts for the transfer hydrogenation of aromatic ketones
Aydemir, Murat,Baysal, Akin,Guemguem, Bahattin
, p. 1 - 8 (2012)
The ability of transition metal catalysts to add or remove hydrogen from organic substrates by transfer hydrogenation is a valuable synthetic tool. Towards a series of novel metal complexes with a P-NH ligand, [Ph 2PNHCH2-C4H3O] derived from furfurylamine were synthesized. Reaction of [Ph2PNHCH 2-C4H3O] 1 with [Ru(η6-p-cymene) (μ-Cl)Cl]2, [Ru(η6-benzene)(μ-Cl)Cl] 2, [Rh(μ-Cl)(cod)]2 and [Ir(η5-C 5Me5)(μ-Cl)Cl]2 gave a range of new monodentate complexes [Ru(Ph2PNHCH2-C4H 3O)(η6-p-cymene)Cl2] 2, [Ru(Ph 2PNHCH2-C4H3O)(η6- benzene)Cl2] 3, [Rh(Ph2PNHCH2-C 4H3O)(cod)Cl] 4, and [Ir(Ph2PNHCH 2-C4H30)(η5-C5Me 5)Cl2] 5, respectively. All new complexes were fully characterized by analytical and spectroscopic methods. 31P-{ 1H} NMR, distortionless enhancement by polarization transfer (DEPT) or 1H-13C heteronuclear correlation (HETCOR) experiments were used to confirm the spectral assignments. Following activation by KOH, compounds 2-5 catalyzed the transfer hydrogenation of acetophenone derivatives to 1-phenylethanol derivatives in the presence of iso-PrOH as the hydrogen source. Notably [Ru(Ph2PNHCH2-C4H 3O)(η6-benzene)Cl2] 3 acts as an excellent catalyst, giving the corresponding alcohols in 98-99% yield in 20 min at 82°C (time of flight ≤ 297 h-1 ) for the transfer hydrogenation reaction in comparison to analogous rhodium or iridium complexes. Copyright
Ruthenium, rhodium and iridium complexes of the furfuryl-2-(N- diphenylphosphino)methylamine ligand: Molecular structure and catalytic activity
Kayan, Cezmi,Meric, Nermin,Aydemir, Murat,Baysal, Akin,Elma, Duygu,Ak, Bünyamin,?ahin, Ertan,Gürbüz, Nevin,?zdemir, Ismail
experimental part, p. 142 - 148 (2012/08/28)
The reaction of furfurylamine with two equivalents of PPh2Cl in the presence of Et3N affords furfuryl-2-(N,N-bis(diphenylphosphino) amine), (Ph2P)2NCH2-C4H3O (1). The corresponding ruthenium(II) complex trans-[Ru((PPh2) 2NCH2-C4H3O)2Cl 2] (3) was synthesized by reacting 1 with [Ru(η6-p- cymene)(μ-Cl)Cl]2. The reaction of furfurylamine with one equivalent of PPh2Cl gives Ph2PNHCH2-C 4H3O (2). The reaction of 2 with [Ru(η6-p- cymene)(μ-Cl)Cl]2, [Ru(η6-benzene)(μ-Cl)Cl] 2, [Rh(μ-Cl)(cod)]2 and [Ir(η5-C 5Me5)(μ-Cl)Cl]2 yields the complexes [Ru(Ph2PNHCH2-C4H3S) (η6-p-cymene)Cl2] (4), [Ru(Ph2PNHCH 2-C4H3O)(η6-benzene)Cl 2] (5), [Rh(Ph2PNHCH2-C4H 3O)(cod)Cl] (6) and [Ir(Ph2PNHCH2-C 4H3O)(η5-C5Me 5)Cl2] (7), respectively. All the complexes were isolated from the reaction solution and fully characterized by analytical and spectroscopic methods. The structure of [Ru(Ph2PNHCH 2-C4H3O)(η6-p-cymene)Cl 2] (4) was also determined by single crystal X-ray diffraction. Complexes 3-7 are suitable precursors forming highly active catalysts in the transfer hydrogenation of a variety of simple ketones. Notably, the catalysts obtained by using the ruthenium complexes [Ru(Ph2PNHCH 2-C4H3O)(η6-p-cymene)Cl 2] (4) and [Ru(Ph2PNHCH2-C4H 3O)(η6-benzene)Cl2] (5) are much more active in the transfer hydrogenation, converting the carbonyls to the corresponding alcohols in 97-99% yields (TOF ≤300 h-1), compared to analogous rhodium and iridium complexes and the trans-Ru(II)-p-cymene bis(phosphino)amine complex.
Aminophosphine-palladium(II) complexes: Synthsesis, structure and applications in Suzuki and Heck cross-coupling reactions
Aydemir, Murat,Baysal, Akin,Sahin, Ertan,Gumgum, Bahattin,Ozkar, Saim
experimental part, p. 10 - 18 (2012/02/02)
Reaction of furfurylamine with 1 or 2 equivalents of PPh2Cl in the presence of Et3N, proceeds under anaerobic conditions in thf to give furfuryl-2-(N-diphenylphosphino)amine, Ph2PNHCH 2-C4H3/sub
