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Öğe Cross-coupling reactions in water using ionic liquid-based palladium(II)-phosphinite complexes as outstanding catalysts(Wiley, 2014) Meriç, Nermin; Aydemir, Murat; Işık, Uğur; Ocak, Yusuf Selim; Rafikova, Khadichakhan; Paşa, Salih; Kayan, Cezmi; Durap, Feyyaz; Temel, Hamdi; Zazybin, Alexey G.; 0000-0003-0899-1948; 0000-0002-6244-9327; 0000-0002-4792-8821Two new phosphinite ligands based on ionic liquids [(Ph2PO)C7H14N2Cl]Cl (1) and [(Cy2PO)C7H14N2Cl]Cl (2) were synthesized by reaction of 1-(3-chloro-2-hydoxypropyl)-3-methylimidazolium chloride, [C7H15N2OCl]Cl, with one equivalent of chlorodiphenylphosphine or chlorodicyclohexylphosphine, respectively, in anhydrous CH2Cl2 and under argon atmosphere. The reactions of 1 and 2 with MCl2(cod) (M=Pd, Pt; cod=1,5-cyclooctadiene) yield complexes cis-[M([(Ph2PO)C7H14N2Cl]Cl)(2)Cl-2] and cis-[M(Cy2PO)C7H14N2Cl]Cl)(2)Cl-2], respectively. All complexes were isolated as analytically pure substances and characterized using multi-nuclear NMR and infrared spectroscopies and elemental analysis. The catalytic activity of palladium complexes based on ionic liquid phosphinite ligands 1 and 2 was investigated in Suzuki cross-coupling. They show outstanding catalytic activity in coupling of a series of aryl bromides or aryl iodides with phenylboronic acid under the optimized reaction conditions in water. The complexes provide turnover frequencies of 57 600 and 232 800h(-1) in Suzuki coupling reactions of phenylboronic acid with p-bromoacetophenone or p-iodoacetophenone, respectively, which are the highest values ever reported among similar complexes for Suzuki coupling reactions in water as sole solvent in homogeneous catalysis. Furthermore, the palladium complexes were also found to be highly active catalysts in the Heck reaction affording trans-stilbenes. Copyright (c) 2014 John Wiley & Sons, Ltd.Öğe 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(Elsevier B.V., 2023) Işık, Uğur; Meriç, Nermin; Kayan, Cezmi; Kılıç, Ahmet; Belyankova, Yelizaveta; Zazybin, Alexey G.; Aydemir, MuratTwo 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.