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    Aminophosphine-palladium(II) complexes: Synthsesis, structure and applications in Suzuki and Heck cross-coupling reactions
    (Elsevier Science Sa, 2011) Aydemir, Murat; Baysal, Akin; Sahin, Ertan; Gumgum, Bahattin; Ozkar, Saim
    Reaction of furfurylamine with 1 or 2 equivalents of PPh2Cl in the presence of Et3N, proceeds under anaerobic conditions in thf to give furfuryl-2-(N-diphenylphosphino)amine, Ph2PNHCH2-C4H3O, 1 and furfuryl-2-(N,N-bis(diphenylphosphino)amine), (Ph2P)(2)NCH2-C4H3O, 2, respectively. The reactions of 1 and 2 with MCl2(cod) (M = Pd, Pt; cod = 1,5-cyclooctadiene) or Pt(CH3)(2)(cod) yield complexes [M(Ph2PNHCH2-C4H3O)(2)Cl-2] (M= Pd 1a, Pt 1b), [Pt(Ph2PNHCH2-C4H3O)(2)(CH3)(2)] (1c), and [M((Ph2P)(2) NCH2-C4H3O)Cl-2] (M= Pd 2a, Pt 2b), [Pt((Ph2P)(2)NCH2-C4H3O)(CH3)(2)] (2c), respectively. All the compounds were isolated as analytically pure substances and characterized by NMR, IR spectroscopy and elemental analysis. Representative solid-state structures of 2a and 2b were also determined by X-ray single crystal diffraction technique. Furthermore, the palladium complexes 1a and 2a were tested and found to be highly active catalysts in the Suzuki coupling and Heck reaction affording biphenyls and trans-stilbenes, respectively. (C) 2011 Elsevier B.V. All rights reserved.
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    Öğe
    Organometallic ruthenium, rhodium and iridium complexes containing a P-bound thiophene-2-(N-diphenylphosphino)methylamine ligand: Synthesis, molecular structure and catalytic activity
    (Elsevier Science Sa, 2011) Aydemir, Murat; Baysal, Akin; Meric, Nermin; Kayan, Cezmi; Gumgum, Bahattin; Ozkar, Saim; Sahin, Ertan
    Reaction of Ph2PNHCH2-C4H3S with [Ru(eta(6)-p-cymene)(mu-Cl)Cl](2), [Ru(eta(6)-benzene)(mu-Cl)Cl](2), [Rh(mu-Cl)(cod)](2) and [Ir(eta(5)-C5Me5)(mu-Cl)Cl](2) yields complexes [Ru(Ph2PNHCH2-C4H3S)(eta(6)-p-cymene)Cl-2], 1, [Ru(Ph2PNHCH2-C4H3S)(eta(6)-benzene)Cl-2], 2, [Rh(Ph2PNHCH2-C4H3S)(cod)Cl], 3 and [Ir(Ph2PNHCH2-C4H3S)(eta(5)-C5Me5)Cl-2], 4, respectively. All complexes were isolated from the reaction solution and fully characterized by analytical and spectroscopic methods. The structure of [Ru(Ph2PNHCH2-C4H3S)(eta(6)-benzene)Cl-2], 2 was also determined by single crystal X-ray diffraction. 1-4 are suitable precursors forming highly active catalyst in the transfer hydrogenation of a variety of simple ketones. Notably, the catalysts obtained by using the ruthenium complexes [Ru(Ph2PNHCH2-C4H3S)(eta(6)-p-cymene)Cl-2], 1 and [Ru(Ph2PNHCH2-C4H3S)(eta(6)-benzene)Cl-2], 2 are much more active in the transfer hydrogenation converting the carbonyls to the corresponding alcohols in 98-99% yields (TOF <= 200 h(-1)) in comparison to analogous rhodium and iridium complexes. (C) 2011 Elsevier B.V. All rights reserved.
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    Öğe
    Ruthenium, rhodium and iridium complexes of the furfuryl-2-(N-diphenylphosphino)methylamine ligand: Molecular structure and catalytic activity
    (Pergamon-Elsevier Science Ltd, 2012) Kayan, Cezmi; Meric, Nermin; Aydemir, Murat; Baysal, Akin; Elma, Duygu; Ak, Bunyamin; Sahin, Ertan
    The reaction of furfurylamine with two equivalents of PPh2Cl in the presence of Et3N affords furfuryl-2-(N,N-bis(diphenylphosphino)amine), (Ph2P)(2)NCH2-C4H3O (1). The corresponding ruthenium(II) complex trans-[Ru((PPh2)(2)NCH2-C4H3O)(2)Cl-2] (3) was synthesized by reacting 1 with [Ru(eta(6)-p-cymene)(mu-Cl)Cl](2). The reaction of furfurylamine with one equivalent of PPh2Cl gives Ph2PNHCH2-C4H3O (2). The reaction of 2 with [Ru(eta(6)-p-cymene)(mu-Cl)Cl](2), [Ru(eta(6)-benzene)(mu-Cl)Cl](2), [Rh(mu-Cl)(cod)](2) and [Ir(eta(5)-C5Me5)(mu-Cl)Cl](2) yields the complexes [Ru(Ph2PNHCH2-C4H3S)(eta(6)-p-cymene)Cl-2] (4), [Ru(Ph2PNHCH2-C4H3O)(eta(6-)benzene)Cl-2] (5), [Rh(Pb2PNHCH2-C4H3O)(cod)Cl] (6) and [Ir(Ph2PNHCH2-C4H3O)(eta(5)-C5Me5)Cl-2] (7), respectively. All the complexes were isolated from the reaction solution and fully characterized by analytical and spectroscopic methods. The structure of [Ru(Ph2PNHCH2-C4H3O)(eta(6)-p-cymene)Cl-2] (4) was also determined by single crystal X-ray diffraction. Complexes 3-7 are suitable precursors forming highly active catalysts in the transfer hydrogenation of a variety of simple ketones. Notably, the catalysts obtained by using the ruthenium complexes [Ru(Ph2PNHCH2-C4H3O)(eta(6)-p-cymene)Cl-2] (4) and [Ru(Ph2PNHCH2-C4H3O)(eta(6)-benzene)Cl-2] (5) are much more active in the transfer hydrogenation, converting the carbonyls to the corresponding alcohols in 97-99% yields (TOF <= 300 h(-1)), compared to analogous rhodium and iridium complexes and the trans-Ru(II)-p-cymene bis(phosphino)amine complex. (c) 2012 Elsevier Ltd. All rights reserved.
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    Synthesis and X-ray crystal structures of three new terpyridine-based Pb(II) complexes, cytotoxicity studies of {[Pb(ttpy)(?-AcO)]2}(SCN)2
    (Taylor & Francis Ltd, 2014) Saghatforoush, Lotfali; Sahin, Ertan; Babaei, Somayyeh; Bakhtiari, Akbar; Nasimian, Ahmad; Celik, Omer; Zabihollahi, Zohreh
    Synthesis and X-ray crystal structures of three new terpyridine-based Pb(II) complexes, {[Pb(ttpy)(mu-AcO)](2)}(SCN)(2) (1) (ttpy = 4'-tolyl-2,2': 6',2 ''-terpyridine), [Pb(Clphtpy)(AcO)(ClO4)] (2), and [Pb(Clphtpy)(SCN)(2)] (3) (Clphtpy = 4'-(4-chlorophenyl)-2,2': 6',2 ''-terpyridine), are described. The synthesized materials have been characterized, also, by CHN elemental analysis, H-1 NMR, and IR spectroscopy. The structural analyses showed that, in the solid state, the coordination number of Pb(II) in 1, 2, and 3 are six, seven, and five, respectively. In the complexes, the lone-pair electrons of Pb(II) are stereochemically active and the coordination geometry of Pb(II) is hemidirected. The structures of the three complexes were compared and the effect of counter ion is described. The antibacterial activity of 1 and previously reported {[Pb(ttpy)(mu-AcO)](2)}(PF6) 2 (1A) and {[Pb(ttpy)(mu-AcO)I](2)} (1B) were tested by minimum inhibitory concentration method to investigate the effect of counter ions on biological activity of the compounds. Also, cytotoxicity test was assessed using 3-[4,5-dimethylthiazol-2-yl]-2,5 diphenyl tetrazolium bromide assay to determine the maximum non-toxic concentration of ttpy, Pb(II), and their complexes to HepG2 cells. Effective lead detoxification was observed for 1, 1A, and 1B.