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    Asymmetric transfer hydrogenation of alkyl/aryl or alkyl/methyl ketones catalyzed by known C2-symmetric ferrocenyl-based chiral bis(phosphinite)-Ru(II), Rh(I) and Ir(III) complexes
    (Elsevier Science Sa, 2016) Durap, Feyyaz; Karakas, Duygu Elma; Ak, Bunyamin; Baysal, Akin; Aydemir, Murat
    Known Ru(II), Rh(I) and Ir(III) complexes of C-2-symmetric ferrocenyl based chiral bis(phoshinite) ligands were catalyzed the asymmetric transfer hydrogenation of alkyl/aryl or alkyl methyl ketones. Corresponding secondary alcohols were obtained with high enantioselectivities up to 98% ee and reactivities using iso-propanol as the hydrogen source. (C) 2016 Elsevier B.V. All rights reserved.
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    Chiral C2-symmetric ?6-p-cymene-Ru(II)-phosphinite complexes: Synthesis and catalytic activity in asymmetric reduction of aromatic, methyl alkyl and alkyl/aryl ketones
    (Elsevier Science Sa, 2018) Karakas, Duygu Elma; Aydemir, Murat; Durap, Feyyaz; Baysal, Akin
    Chiral C-2-symmetric bis(phosphinite) ligands and their binuclear ruthenium(II) complexes have been synthesized and used as catalysts in the ruthenium-catalyzed asymmetric transfer hydrogenation of aromatic, methyl alkyl and alkyl/aryl ketones using 2-propanol as both the hydrogen source and solvent in the presence of KOH. Under optimized conditions, all complexes showed high catalytic activity as catalysts in the reduction of various ketones to corresponding chiral secondary alcohols. Products were obtained with high conversions (99%) and moderate to good enantioselectivities (82% ee). Furthermore, C2-symmetric bis(phosphinite) ligands and their binuclear ruthenium(II) complexes were characterized by multinuclear NMR spectroscopy, FT-IR spectroscopy, LC/MS-MS and elemental analysis. (C) 2017 Elsevier B.V. All rights reserved.
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    Chiral phosphinites as efficient ligands for enantioselective Ru(II), Rh(I) and Ir(III)-catalyzed transfer hydrogenation reactions
    (Springer, 2017) Baysal, Akin; Karakas, Duygu Elma; Meric, Nermin; Ak, Bunyamin; Aydemir, Murat; Durap, Feyyaz
    Metal-catalyzed enantioselective transfer reduction of ketones to enantiomerically enriched chiral alcohols has recently attracted attention. Therefore, a series of methyl alkyl or alkyl/aryl ketones have been reduced by using Ru(II), Rh(I) and Ir(III) catalysts based on C (2)-symmetric chiral ferrocenyl phosphinite ligands. The corresponding optically active secondary alcohols were obtained in excellent conversions and moderate-to-good enantioselectivities. The best results were obtained with an iridium catalyst, giving up to 98% conversion and 80% ee.
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    Ferrocene based chiral binuclear ?6-benzene-Ru(II)-phosphinite complexes: Synthesis, characterization and catalytic activity in asymmetric reduction of ketones
    (Wiley, 2018) Al-bayati, Yaser W. Abdlhmed; Karakas, Duygu Elma; Meric, Nermin; Aydemir, Murat; Durap, Feyyaz; Baysal, Akin
    In the present study, a series of chiral C-2-symmetric ferrocenyl based binuclear (6)-benzene-Ru(II) complexes bearing diphenylphosphinite and diisopropylphosphinite moieties have been synthesised. The new binuclear (6)-benzene-Ru(II)-phosphinite complexes were characterised based on nuclear magnetic resonance (H-1, C-13, P-31-NMR), FT-IR spectroscopy and elemental analysis. Then, these complexes have been screened as catalytic precursors in the transfer hydrogenation of acetophenone with 2-propanol as both the hydrogen source and solvent in the presence of KOH. The corresponding optically active secondary alcohols were obtained in excellent conversion rates between 96 and 99% and moderate to good enantioselectivities (up to 78% ee). The complex 5 was the most efficient catalyst among the four new complexes investigated herein.
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    Integrated Catalytic and Energy Storage Performance of Grass Waste Derived Ni-Based Catalyst
    (Springer Heidelberg, 2024) Karakas, Duygu Elma; Horoz, Sabit; Durap, Feyyaz; Orak, Ceren; Kaya, Mustafa
    This study focuses on the optimization and characterization of a grass waste-derived catalyst, GW-Ni-Cat, for hydrogen generation via NaBH4 methanolysis, as well as its application in supercapacitors. Optimization experiments were conducted to determine the optimal conditions for acid concentration, metal concentration, carbonization temperature, and carbonization time. The catalyst was characterized using various techniques including FTIR, XRD, SEM, TEM, BET, and ICP-OES. Performance experiments demonstrated the catalyst's efficiency in hydrogen generation, with key factors such as catalyst amount, NaBH4 concentration, and temperature influencing the reaction kinetics. Reusability tests showed the catalyst's stability over multiple cycles. Electrochemical characterization revealed the suitability of GW-Ni-Cat as an electrode material for supercapacitors, with high specific capacitance values. Comparison with other bio-based supercapacitors demonstrated the superior performance of GW-Ni-Cat. Overall, this study presents GW-Ni-Cat as a versatile and efficient material for both hydrogen generation and energy storage applications.
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    Novel ruthenium and palladium complexes as potential anticancer molecules on SCLC and NSCLC cell lines
    (Springer International Publishing Ag, 2020) Tokgun, Onur; Karakas, Duygu Elma; Tan, Semih; Karagur, Ege Riza; Inal, Behcet; Akca, Hakan; Durap, Feyyaz
    Lung cancer is one of the major causes of cancer-related deaths in the world. Non-small-cell lung cancer (NSCLC) is the most common type of lung cancer, and small-cell lung cancer (SCLC) is the most aggressive subtype of lung cancer. Proper therapies for SCLC have not yet been developed. However, new molecules have been designed and big innovation in treating SCLC has been achieved. Platinum-based antitumor drugs like cisplatin and carboplatin have several disadvantages including side effects, cisplatin-resistant tumors and limited solubility in aqueous media. Thus, two novel chiral aminoalcohol-based bis(phosphinite) ligands containing (eta(6)-p-cymene)-Ru(II)-phosphinite and bis(phosphinite)-Pd(II) complexes were synthesized and evaluated for anticancer activity. In this study, the results showed that complex1has the strongest cytotoxic effects on SCLC and NSCLC cell lines. On the other hand, cisplatin, ruthenium and palladium complexes are capable to induce apoptosis. Especially, complexes1and2can induce apoptosis for both SCLC and NSCLC. When compared to the qRT-PCR and TUNEL results, we obtained a significant correlation between apoptotic index and p21, Bax gene expressions. This work revealed the potential of the synthesized complexes as anticancer agents with cytotoxic and pro-apoptotic activity as leading compounds for further anticancer researches.
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    Synthesis of cis-1,2-diol-type chiral ligands and their dioxaborinane derivatives: Application for the asymmetric transfer hydrogenation of various ketones and biological evaluation
    (Wiley, 2020) Kilic, Ahmet; Balci, Tubba Ersayan; Arslan, Nevin; Aydemir, Murat; Durap, Feyyaz; Okumu, Veysi; Tekin, Recep
    Two cis-1,2-diol-type chiral ligands (T-1 and T-2) and their tri-coordinated chiral dioxaborinane (T(1-2)B(1-2)) and four-coordinated chiral dioxaborinane adducts with 4-tert-butyl pyridine sustained by N -> B dative bonds (T(1-2)B(1-2)-N) were synthesized and characterized by various spectroscopic techniques such as NMR (H-1, C-13, and B-11), FT-IR and UV-Vis spectroscopy, LC-MS/MS, and elemental analysis. It was suggested that both ferrocene and trifluoromethyl groups played key roles in the catalytic and biological studies because they could tune the solubility of the chiral dioxaborinane complexes and adjust the strength of intermolecular interactions. To assess the biological activities of newly synthesized chiral dioxaborinane compounds, DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging, reducing power, antibacterial, DNA binding, and DNA cleavage activities were tested. Then, all chiral dioxaborinane complexes were investigated as catalysts for the asymmetric transfer hydrogenation of various ketones under suitable conditions. The results indicated that the chiral dioxaborinane catalysts performed well with high yields.
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    Synthesis of ionic liquid-based Ru(II)-phosphinite complexes and evaluation of their antioxidant, antibacterial, DNA-binding, and DNA cleavage activities
    (Springer International Publishing Ag, 2019) Meric, Nermin; Kayan, Cezmi; Rafikova, Khadichakhan; Zazybin, Alexey; Okumus, Veysi; Aydemir, Murat; Durap, Feyyaz
    Two Ru(II) complexes were synthesized by reaction of phosphinite-functionalized imidazolium salts [(Ph2PO)C7H11N2Cl]Cl (1) and [(Cy2PO)C7H11N2Cl]Cl (2) with 1/2 equivalent of [Ru(eta(6)-p-cymene)(mu-Cl)Cl](2) in anhydrous CH2Cl2 and under argon atmosphere. The complexes were then isolated as analytically pure substances and characterized using multinuclear NMR and infrared spectroscopies and elemental analysis. The Ru(II) compounds were used to study their biological assay. For this purpose, radical scavenging, reducing power, antibacterial activity, DNA binding, and DNA cleavage activity were fully studied. The maximum 1,1-diphenyl-2-picrylhydrazyl radicals (DPPH) scavenging (78.9%) and reducing power were obtained from compound 4 at the concentration of 200 mu g/ml. The compounds were also tested against three Gram-positive and three Gram-negative bacteria, and they were found to be more effective against Gram-positive bacteria. In addition, both compounds showed excellent DNA binding and DNA cleavage activity.
  • Küçük Resim
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    Synthesis of ionic liquid‑based Ru(II)–phosphinite complexes and evaluation of their antioxidant, antibacterial, DNA‑binding, and DNA cleavage activities
    (Chemical Papers, 2019) Meriç, Nermin; Kayan, Cezmi; Rafikova, Khadichakhan; Zazybin, Alexey; Okumuş, Veysi; Aydemir, Murat; Durap, Feyyaz
    Two Ru(II) complexes were synthesized by reaction of phosphinite-functionalized imidazolium salts [(Ph2PO)C7H11N2Cl] Cl (1) and [(Cy2PO)C7H11N2Cl]Cl (2) with 1/2 equivalent of [Ru(η6-p-cymene)(μ-Cl)Cl]2 in anhydrous CH2Cl2 and under argon atmosphere. The complexes were then isolated as analytically pure substances and characterized using multinuclear NMR and infrared spectroscopies and elemental analysis. The Ru(II) compounds were used to study their biological assay. For this purpose, radical scavenging, reducing power, antibacterial activity, DNA binding, and DNA cleavage activity were fully studied. The maximum 1,1-diphenyl-2-picrylhydrazyl radicals (DPPH) scavenging (78.9%) and reducing power were obtained from compound 4 at the concentration of 200 μg/ml. The compounds were also tested against three Gram-positive and three Gram-negative bacteria, and they were found to be more effective against Gram-positive bacteria. In addition, both compounds showed excellent DNA binding and DNA cleavage activity.
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    Synthesis of new boron complexes: application to transfer hydrogenation of acetophenone derivatives
    (Wiley-Blackwell, 2011) Kilic, Ahmet; Kayan, Cezmi; Aydemir, Murat; Durap, Feyyaz; Durgun, Mustaf; Baysal, Akin; Tas, Esref
    Two new boron complexes were synthesized from N-[3-(methylmercapto)aniline]-3,5-di-tert-butylsalicylaldimine (LH) with boron reagent BPh3 or BF3 center dot Et2O. These boron complexes are stable and easily soluble in protic solvents such as ethanol (C2H5OH) but hardly soluble in nonprotic solvents such as chloroform (CHCl3), dichloromethane (CH2Cl2) and tetrahydrofuran (THF). All new boron complexes have been fully characterized by both analytical and spectroscopic methods. The catalytic activities of complexes [LBPh2], 2, and [LBF2], 3, in the transfer hydrogenation of acetophenone derivatives were tested. Stable boron complexes were found to be efficient catalysts in the transfer hydrogenation of aromatic ketones in good conversions up to 99% in the presence of iso-PrOH/KOH. Copyright (C) 2011 John Wiley & Sons, Ltd.
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    SYNTHESIS OF NOVEL BIS(PHOSPHINO)AMINE-RUII(ACAC)2 COMPLEXES, AND INVESTIGATION OF CATALYTIC ACTIVITY IN TRANSFER HYDROGENATION
    (2022) Karakas, Duygu Elma; Işık, Uğur; Aydemir, Murat; Durap, Feyyaz; Baysal, Akın
    In this study, reactions of (PPh2)2NCH2CH2N(PPh2)2 (L1) and {(PPh2)2NCH2CH2}3N (L2) with [RuII(acac)2(CH3CN)2] led to the production of new dinuclear complex [Ru(acac)2]2(L1) (1) and trinuclear complex [Ru(acac)2]3(L2) (2). Complex 1 and 2 are excellent candidates for the role of catalyst precursors in the transfer hydrogenation (TH) of acetophenone and its derivatives. Compared to complex (1), the trinuclear complex (2) is an exceptional catalyst, producing the corresponding alcohols in 98–99% yields in 20 minutes at 80 oC (TOF?300 h-1 ) for the TH process. A comparison of the catalytic properties of the complexes is also briefly discussed. Complex structures have also been characterized by combining nuclear magnetic resonance (NMR), Fourier Transform Infrared (FT-IR), and elemental analysis.
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    Synthesis, characterization and first application of chiral C2-symmetric bis(phosphinite)-Pd(II) complexes as catalysts in asymmetric intermolecular Heck reactions
    (Wiley-Blackwell, 2016) Karakas, Duygu Elma; Durap, Feyyaz; Aydemir, Murat; Baysal, Akin
    A series of new chiral C-2-symmetric bis(phosphinite) ligands and their palladium(II) complexes have been synthesized and for the first time used as catalysts in the palladium-catalysed asymmetric intermolecular Heck coupling reactions of 2,3-dihydrofuran with iodobenzene or aryl triflate. Under optimized conditions, products were obtained with high conversions and moderate to good enantioselectivities. The new C-2-symmetric bis(phosphinite) ligands and their palladium(II) complexes were characterized using multinuclear NMR and Fourier transform infrared spectroscopies and elemental analysis. Copyright (c) 2015 John Wiley & Sons, Ltd.
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    Transfer hydrogenation reaction using novel ionic liquid based Rh(I) and Ir(III)-phosphinite complexes as catalyst
    (Elsevier Science Sa, 2016) Karakas, Duygu Elma; Durap, Feyyaz; Baysal, Akin; Ocak, Yusuf Selim; Rafikova, Khadichakhan; Kaya, Eda Cavus; Zazybin, Alexey
    Hydrogen transfer reduction methods are attracting increasing interest from synthetic chemists in view of their operational simplicity. Thus, interaction of [Rh(mu-Cl)(cod)](2) and Ir(eta(5)-C5Me5)(mu-Cl)Cl](2) with phosphinite ligand [(Ph2PO)-C7H11N2Cl]Cl, 1 gave new monodendate (1-chloro-3-(3-methylimidazolidin1-yl)propan-2-yl diphenylphosphinite chloride) (chloro eta(4)-1,5-cyclooctadiene rhodium(I))], 2 and (1chloro-3-(3-methylimidazolidin-1-yl)propan-2-yl diphenylphosphinite chloride) (dichloro n.5-pentamethylcyclopentadienyl iridium(III))1, 3 complexes, which were characterized by a combination of multinuclear NMR spectroscopy, IR spectroscopy, and elemental analysis. H-1-{P-31}NMR, H-1-C-13 HETCOR or H-1-H-1 COSY correlation experiments were used to confirm the spectral assignments. The novel catalysts were applied to transfer hydrogenation of acetophenone derivatives using 2-propanol as a hydrogen source. The results showed that the corresponding alcohols could be obtained with high activity (up to 99%) under mild conditions. Notably, (1-chloro-3-(3-methylimidazolidin-1-yl)propan-2-y1 diphenylphosphinite chloride) (chloro eta(4)-1,5-cyclooctadiene rhodium(I))], 2 complex is much more active than the other analogous complex, 3 in the transfer hydrogenation. Furthermore, compound, 2 acts as excellent catalysts, giving the corresponding alcohols in 97-99% conversions in 5 min (TOF <= 1176 h(-1)). (C) 2016 Elsevier B.V. All rights reserved.