Synthesis of half-sandwich ruthenium(II) and iridium(III) complexes containing imidazole-based phosphinite ligands and their use in catalytic transfer hydrogenation of acetophenone with isopropanol
Işık U. Meriç N. Kayan C. Kılıç A. Belyankova Y. Zazybin A. Aydemir M.
1 October 2023Elsevier B.V.
Journal of Organometallic Chemistry
2023#998
Two ionic liquids (3-(3‑chloro-2-hydroxypropyl)-1-vinyl-1H-imidazol-3-ium chloride and 3-(3‑chloro-2-hydroxypropyl)-1‑butyl‑1H-imidazol-3-ium chloride) were prepared from commercially available, inexpensive 1-vinyl imidazole or 1‑butyl imidazole, respectively, in ethanol at room temperature. Then, these ionic liquids were treated with PPh2Cl to obtain ionic liquid-based phosphinite ligands and the reaction of these phosphinites with [Ru(η6-benzene)(μ-Cl)Cl]2, [Ru(η6−p-cymene)(μ-Cl)Cl]2, or [Ir(η5-C5Me5)(μ-Cl)Cl]2 gave the corresponding ruthenium and iridium complexes. Structures of the synthesized compounds were clarified by multinuclear NMR and IR spectroscopy as well as microanalysis. Furthermore, the complexes were applied as catalysts in the transfer hydrogenation of acetophenone derivatives to afford the corresponding alcohols with high conversions. Notably, [Ru(Ph2PO–C8H11N2Cl2)(η6-benzene)Cl2] acts as a good catalyst, giving the corresponding alcohols in 97–98% yields in 15 min at 82 °C (TOF ≤ 400 h−1) for the transfer hydrogenation reaction in comparison to analogous complexes. The catalysts are also useful for a variety of related ketone substrates with various electronic and steric regulating groups.
Catalysis , Ionic liquid , Ketone reduction , Transfer hydrogenation , Transition metals
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Medical-Aromatic Plants Application and Research Center, Artvin Coruh University, Artvin, 08100, Turkey
Faculty of Science, Department of Chemistry, Dicle University, Diyarbakır, 21280, Turkey
Technical Vocational School, Department of Hair Care and Beauty Services, Dicle University, Diyarbakir, 21280, Turkey
Faculty of Science and Art, Department of Chemistry, Harran University, Şanlıurfa, 63160, Turkey
School of Chemical Engineering, Kazakh-British Technical University, Almaty, 050000, Kazakhstan
Medical-Aromatic Plants Application and Research Center
Faculty of Science
Technical Vocational School
Faculty of Science and Art
School of Chemical Engineering
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