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    C-C coupling formation using nitron complexes
    (Royal Soc Chemistry, 2020) Sevim, Mehmet; Kavukcu, Serdar Batikan; Kinal, Armagan; Sahin, Onur; Turkmen, Hayati
    A series of Ru-II (1), Rh-III (2), Ir-III (3, 4), Ir-I (5) and Pd-II (6-9) complexes of the 'instant carbene' nitron were prepared and characterized by H-1- and C-13-NMR, FT-IR and elemental analysis. The molecular structures of complexes 1-4 and 6 were determined by X-ray diffraction studies. The catalytic activity of the complexes (1-9) was evaluated in alpha(alpha)-alkylation reactions of ketones with alcohol via the borrowing hydrogen strategy under mild conditions. These complexes were able to perform this catalytic transformation in a short time with low catalyst and base amounts under an air atmosphere. Also, the Pd-II-nitron complexes (6-9) were applied in the Suzuki-Miyaura C-C coupling reaction and these complexes successfully initiated this reaction in a short time (30 minutes) using the H2O/2-propanol (1.5 : 0.5) solvent system. The DFT calculations revealed that the Pd-0/II/0 pathway was more preferable for the mechanism.
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    Comparison of Ru(II)-arene complexes containing naphthyl-/ quinolinyl-substituted ligand vis-a-vis structure, spectra and catalytic activity
    (Elsevier, 2024) Turkmen, Gulsah; Cakir, Sinem; Kavukcu, Serdar Batikan; Sahin, Onur; Turkmen, Hayati
    A series of ligands with naphthyl/quinolinyl substituent in their principal molecular framework were synthesised. Their corresponding half -sandwich ruthenium (Ru) complexes ( Ru 1a-b , Ru 2a-b and Ru 3 ) were then successfully generated. The structure of all synthesised compounds was comprehensively elucidated via 1 H and 13 C nuclear magnetic resonance (NMR), elemental analysis and Fourier -transform infrared spectroscopies. Notably, the structural configuration of Ru 3 was delineated via X-ray diffraction. The catalytic efficacy of the Ru complexes was systematically probed in two distinct reactions: 1) transfer hydrogenation (TH) of ketones using 2-propanol as the hydrogen source and 2) reduction of nitroarenes to anilines using sodium tetrahydridoborate as the reducing agent in ethanol, conducted at ambient temperature. Comparative analysis of catalytic yields of the Ru complexes ( Ru 1a-b , Ru 2a-b and Ru 3 ) in both reaction types revealed that Ru 3 delivered superior catalytic performance in both types of reactions. Furthermore, scrutiny of the 1 H NMR spectrum during the TH reaction revealed formation of Ru-hydride species.
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    N-Alkylation and N-Methylation of Amines with Alcohols Catalyzed by Nitrile-Substituted NHC-Ir(III) and NHC-Ru(II) Complexes
    (Amer Chemical Soc, 2023) Cakir, Sinem; Kavukcu, Serdar Batikan; Sahin, Onur; Gunnaz, Salih; Turkmen, Hayati
    A series of nitrile-modified N-heterocyclic carbene (NHC) complexes of Ir(III) (2a-e) and Ru(II) (3a-d) have been prepared by transmetallation of [IrCp*Cl2]2 and [RuCl2(p-cymene)]2 forming an in situ NHC-Ag complex. The structures of all complexes were characterized by 1H NMR, 13C NMR, and Fourier transform infrared (FT-IR) spectroscopies. And the structures were clearly elucidated by performing X-ray diffraction studies on 2b, 3a, and 3c single crystals. The complexes of NHC- Ir(III) (2a-e) and NHC-Ru(II) (3a-d) were investigated in the N-alkylation reaction of aniline derivatives with benzyl alcohols to form N-benzyl amines and in the N-methylation reaction of aniline derivatives with methanol. Both reactions were performed in solvent-free media. The Ir(III) complexes (2a-e) were found to perform essentially better than similar Ru(II) complexes (3a-d) in the N-alkylation and N-methylation reactions. Among the Ir(III) complexes (2a-e), the best results were obtained with 2b. The catalytic mechanisms of both reactions were revealed by 1H NMR study. Formation of Ir-hydride species was observed for both reactions. This new report provides useful information to evaluate the activity of complexes and the differences in sensitivity between the NHCs.
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    Piano-stool Ru (II) arene complexes that contain ethylenediamine and application in alpha-alkylation reaction of ketones with alcohols
    (Wiley, 2019) Kavukcu, Serdar Batikan; Gunnaz, Salih; Sahin, Onur; Turkmen, Hayati
    A series of piano-stool Ru (II) complexes (Ru1-7) bearing ethylenediamine with aryl and aliphatic groups were prepared and fully characterized by H-1, C-13, F-19 and P-31 NMR spectroscopy, FT-IR and elemental analysis. The crystal structures of Ru2-4 and Ru-7 were determined by X-ray crystallography. They were successfully applied to the alpha(alpha)-alkylation of aliphatic and aromatic ketones with alcohols via the borrowing hydrogen strategy in mild reaction conditions within a short time. The catalytic system has a broad substrate scope, which allows the synthesis of alpha alkylated ketones with excellent yields. The electronic and steric effects of complexes on catalytic activity were analysed. The influence of the carbon chain length of the ligand on the alpha-alkylation reaction of ketones was also investigated. The catalytic cycle was also examined by H-1-NMR spectroscopy in d(8)-toluene.
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    Synthesis and catalytic applications of Ru and Ir complexes containing N,O-chelating ligand
    (Elsevier Science Sa, 2020) Pakyapan, Bilge; Kavukcu, Serdar Batikan; Sahin, Zarife Sibel; Turkmen, Hayati
    A series of monometallic complexes (Ru1-3, Ir-1(-3)) which have N,O-chelating ligand (pyrazine-2carboxylate (1), pyridine-2-carboxylate (2), quinoline carboxylate(3) and bimetallic complexes (Ru-4,Ru-5, Ir-4(,5)) bridged by pyrazine-2,3- dicarboxylate (4) and imidazole-4,5-dicarboxylate(5) were synthesized and characterized by H-1-, C-13 NMR, FT-IR, and elemental analysis. The crystal structure of Ir-2 was determined by X-ray crystallography. The complexes (Ru1-5, Ir1-5) were applied to investigate the electronic and steric effect of ligand in their catalytic activities in transfer hydrogenation and alpha(alpha)-alkylation reaction of ketones with alcohols. The activities of iridium complexes (Ir1-5) were much more efficient than ruthenium complexes (Ru1-5). The highest activity for both reactions was observed for the complex (Ir2 ) with pyridine-2-carboxylate. The Ir hydride species was monitored for both reactions. (C) 2020 Elsevier B.V. All rights reserved.
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    Synthesis and cytotoxic activities of organometallic Ru(II) diamine complexes
    (Academic Press Inc Elsevier Science, 2020) Kavukcu, Serdar Batikan; Sahin, Onur; Vatansever, Hafize Seda; Kurt, Feyzan Ozdal; Korkmaz, Mehmet; Kendirci, Remziye; Pelit, Levent
    A series of mono and bimetallic ruthenium(II) arene complexes bearing diamine (Ru1-6) were prepared and fully characterized by H-1, C-13, F-19, and P-31 NMR spectroscopy and elemental analysis. The crystal structure of the bimetallic complex (Ru-5) was determined by X-ray crystallography. Monometallic analogues (Ru1-3) were synthesized to investigate the contributions of ruthenium and the other organic groups (aren, ethylenediamine, butyl) to the activity. The electrochemical behaviors of mono and bimetallic complexes were obtained from the relationship between cyclic voltammetry (CV) and the biological activities of the compounds. The cytotoxic activities of the complexes (Ru1-6) were tested against wide-scale cancer cell lines, namely HeLa, MDA-MB-231, DU-145, LNCaP, Hep-G2, Saos-2, PC-3, and MCF-7, and normal cell lines 3T3-L1 and Vero. Diamine Ru(II) arene complexes have unique biological characteristics and they are promising models for new anticancer drug development. MTT analysis reveals that each synthesized Ru complex showed cytotoxic activity towards the different cancer cells. In particular, three Ru complexes (Ru-3, Ru-5 and Ru-6) showed less toxic effects on the cancer cells than the others. These novel Ru complexes affected both cancer and normal cell lines. As they had a toxic effect on the cells, the dosage applied should be tested before being used for in vivo applications. Cytotoxicity tests have shown that the bimetallic complex Ru-6 was effective on all cancer cells. The effect of bimetallic enhancement on cancer cell lines, the systematic variation of the intermetallic distance and the ligand donor properties of the mono and bimetallic complexes were explored based on the cytotoxic activity. The interaction with FS-DNA and the stability/aquation of the complexes (Ru-3 and Ru-6) were investigated with H-1 NMR spectroscopy. The binding modes between the complexes (Ru-3 and Ru-6) and DNA were investigated via UV-Vis spectroscopy.