Novel neutral phosphinite bridged dinuclear ruthenium(II) arene complexes and their catalytic use in transfer hydrogenation of aromatic ketones: X-ray structure of a new Schiff base, N3,N3 '-di-2-hydroxybenzylidene-[2,2 ']bipyridinyl-3,3 '-diamine

Date

2010-07-01

Author

AYDEMİR, MURAT
DURAP, FEYYAZ
BAYSAL, AKIN
MERİÇ, NERMİN
Buldag, Ayseguel
Guemguem, Bahattin
Özkar, Saim
Yildirim, Leyla Tatar

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A novel Schiff base N3,N3'-di-2-hydroxybenzylidene-[2,2']bipyridinyl-3,3'-diamine, 1 was synthesized from condensation of salicylaldehyde with 3,3'-diamino-2,2'-bipyridine. Reaction of 1 with two equivalents of PPh(2)Cl in the presence of Et(3)N proceeds in toluene to give N3,N3'-di-2-(diphenylphosphino)benzylidene-[2,2']bipyridinyl-3,3'-diamine, 2 in quantitative yield. Ruthenium(II) dimers [Ru(eta(6)-arene)(mu-Cl)]Cl](2) readily react with phosphinite ligand [(Ph(2)PO)(2)-C(24)H(16)N(4)], 2 in toluene at room temperature, to afford the neutral derivatives [C(24)H(16)N(4){OPPh(2)-Ru(eta(6)-arene)Cl(2}2)] {arene: benzene 3, p-cymene, 4}. All the complexes were fully characterized by analytical and spectroscopic methods. (31)P-{(1)H} NMR, (1)H-(13)C HETCOR or (1)H-(1)H COSY correlation experiments were used to confirm the spectral assignments. Molecular structure of the Schiff base, 1 was also determined by X-ray single crystal diffraction study. The catalytic activity of complexes 3 and 4 in the transfer hydrogenation of acetophenone derivatives was tested. Stable ruthenium(II)-phosphinite complexes were found to be efficient catalysts in the transfer hydrogenation of aromatic ketones in excellent conversions up to 99% (up to 530 per hour) in the presence of iso-PrOH/KOH.

Subject Keywords

Physical and Theoretical Chemistry, Process Chemistry and Technology, Catalysis

URI

https://hdl.handle.net/11511/63037

Journal

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL

DOI

https://doi.org/10.1016/j.molcata.2010.04.010

Collections

Department of Chemistry, Article

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Citation Formats

M. AYDEMİR et al., “Novel neutral phosphinite bridged dinuclear ruthenium(II) arene complexes and their catalytic use in transfer hydrogenation of aromatic ketones: X-ray structure of a new Schiff base, N3,N3 ‘-di-2-hydroxybenzylidene-[2,2 ‘]bipyridinyl-3,3 ’-diamine,” JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, pp. 75–81, 2010, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/63037.