Araştırma Makalesi
BibTex RIS Kaynak Göster

NOVEL MONONUCLEAR METAL-PHOSPHINITE COMPOUNDS AND CATALYTIC PERFORMANCE IN TRANSFER HYDROGENATION OF KETONES

Yıl 2022, Cilt: 8 Sayı: 1, 1 - 15, 17.06.2022
https://doi.org/10.51477/mejs.1077805

Öz

Since the obtained chiral alcohols are rather useful as well as biologically active compounds, reduction of ketones to their respective alcohols is a crucial topic in synthetic chemistry. Thus, a new phosphinite ligand was synthesized by the interaction of cationic species N-vinyl imidazolium (1) with PCy2Cl. This phosphinite ligand in combination with [Ru(η6-p-cymene)(µ-Cl)Cl]2 and Ir(η5-C5Me5)(μ-Cl)Cl]2 gave active catalytic systems for transfer hydrogenation reaction. Under optimum circumstances, ruthenium complex (3) showed rather high conversion reduction reaction of acetophenone. Reversibility of the transfer hydrogenation reaction was found to be low under these reaction circumstances.

Destekleyen Kurum

Dicle University Research Fund

Proje Numarası

FEN.20.001

Teşekkür

Dicle University Research Fund

Kaynakça

  • [ 1] Chauvin, R. 2000. “Zwitterionic Organometallates", Eur. J. Inorg. Chem., 4, 577–591.
  • [ 2] Zhang, H., Li, Y.-Q., Wang, P., Lu, Y., Zhao, X.-L., Liu, Y. 2016. “Effect of positive-charges in diphosphino- imidazolium salts on thestructures of Ir-complexes and catalysis for hydroformylation", Journal of Molecular Catalysis A: Chemical, 411, 337–343.
  • [3 ] Li, Y.Q., Wang, P., Zhang, H., Zhao, X.L., Lu, Y., Popovi´c, Z., Liu, Y. 2015. “Influence of electrostatic repulsive force and electron-withdrawing effect in ionic diphosphine on regioselectivity of rhodium-catalyzed hydroformylation of 1-octene", J. Mol. Catal. A: Chem., 402, 37–45.
  • [ 4] You, H.X., Wang, Y.Y., Zhao, X.L., Chen, S.J., Liu, Y. 2013. “Stable Ionic Rh(I,II,III) Complexes Ligated by an Imidazolium-Substituted Phosphine with π-Acceptor Character: Synthesis, Characterization, and Application to Hydroformylation", Organometallics, 32(9),, 2698–2704.
  • [5 ] Zhang, J., Wang, Y.Y., Zhao, X.L., Liu, Y. 2014. “Phosphane‐Ligated Ionic Palladium Complexes: Synthesis, Characterization and Application as Efficient and Reusable Precatalysts for the Homogeneous Carbonylative Sonogashira Reaction under CuI‐Free Conditions", Eur. J. Inorg. Chem., 2014 (6), 975–985.
  • [6 ] Zhou, C.L., Zhang, J., Ðakovic, M., Popovic, Z., Zhao, X.L., Liu, Y. 2012. “Synthesis of an Ionic Paramagnetic Ruthenium (III) Complex and Its Application as an Efficient and Recyclable Catalyst for the Transfer Hydrogenation of Ketones", Eur. J. Inorg. Chem., 2012 (21), 3435–3440.
  • [ 7] Luska, K.L., Demmans, K.Z., Stratton, S.A., Moores, A. 2012. “Rhodium complexes stabilized by phosphine-functionalized phosphonium ionic liquids used as higher alkene hydroformylation catalysts: influence of the phosphonium headgroup on catalytic activity", Dalton Trans., 41, 13533–13540.
  • [8 ] Canac, Y., Maaliki, C., Abdellahab, I., Chauvin, R. 2012. “Carbeniophosphanes and their carbon → phosphorus → metal ternary complexes", New J. Chem., 36, 17–27.
  • [ 9] Valizadeh, H., Khalili, E. 2012. “Efficient synthesis of symmetrical phthalate and maleate diesters using phosphinite ionic liquids", Iran Chem Soc., 9, 529–534.
  • [10 ] Valizadeh, H., Shockravi, A. 2009 (a). “Imidazolium-Based Phosphinite Ionic Liquid as Reusable Catalyst and Solvent for One- Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-(thio)ones", Heteroatom Chemistry, 20(5), 284-288.
  • [11 ] Valizadeh, H., Shockravi, A. 2009 (b). “Task-Specific Ionic Liquid as Reagent and Reaction Medium for the One-Pot Horner–Wadsworth–Emmons–Type Reaction Under Microwave Irradiation", Synthetic Communications1, 39, 4341–4349.
  • [ 12] Valizadeh, H., Gholipour, H. 2010. “Imidazolium-Based Phosphinite Ionic Liquid (ILOPPh2) as Reusable Catalyst and Solvent for the Knoevenagel Condensation Reaction", Synthetic Communications1, 40, 1477–1485.
  • [ 13] Iranpoor, N. Firouzabadi, H., Azadi, R. 2008. “Imidazolium-based phosphinite ionic liquid (IL-OPPh2) as Pd ligand and solvent for selective dehalogenation or homocoupling of aryl halides", Journal of Organometallic Chemistry, 693, 2469–2472.
  • [ 14] Iranpoor, N. Firouzabadi, H., Azadi, R. 2010. “Diphenylphosphinite ionic liquid (IL-OPPh2): A solvent and ligand for palladium-catalyzed silylation and dehalogenation reaction of aryl halides with triethylsilane", Journal of Organometallic Chemistry, 695, 887–890.
  • [15 ] Iranpoor, N. Firouzabadi, H., Azadi, R. 2007. “An Imidazolium-Based Phosphinite Ionic Liquid (IL-OPPh2) as a Reusable Reaction Medium and PdII Ligand in Heck Reactions of Aryl Halides with Styrene and n-Butyl Acrylate", Eur. J. Org. Chem., 2197–2201.
  • [ 16] Aydemir, M., Rafikova, K., Kystaubayeva, N., Pasa, S., Meriç, N., Ocak, Y. S., Zazybin, A., Temel, H., Gürbüz, N., Özdemir, İ., 2014, “Ionic liquid based Ru(II)–phosphinite compounds and their catalytic use in transfer hydrogenation: X-ray structure of an ionic compound 1-chloro-3-(3-methylimidazolidin-1-yl)propan-2-ol”, Polyhedron, 81, 245–255.
  • [17 ] Elma Karakaş, D., Durap, F., Baysal, A., Ocak, Y. S., Rafikova, K., Çavus Kaya, E., Zazybin, A., Temel, H., Kayan, C., Meriç, N., Aydemir, M., 2016, “Transfer hydrogenation reaction using novel ionic liquid based Rh(I) and Ir(III)-phosphinite complexes as catalyst,” Journal of Organometallic Chemistry, 824, 25-32.
  • [18 ] Meriç, N., Arslan, N., Kayan, C., Rafikova, K., Zazybin, A., Kerimkulova, A., Aydemir, M., 2019, “Catalysts for the asymmetric transfer hydrogenation of various ketones from [3-[(2S)-2-[(diphenylphosphanyl)oxy]-3-phenoxypropyl]-1-methyl-1H-imidazol-3-ium chloride] and [Ru(eta(6)-arene)(mu-Cl)Cl](2), Ir(eta(5)-C5Me5)(mu-Cl)Cl](2) or [Rh(mu-Cl)(cod)](2)”, Inorganica Chimica Acta, 492, 108-118.
  • [19 ] Ojima, I., 2010, Catalytic Asymmetric Synthesis, John Wiley, Hoboken, N.J., ISBN: 978-0-470-17577-4
  • [20 ] Baratta, W., Rigo, P., 2008, “1-(Pyridin-2-yl)methanamine-Based Ruthenium Catalysts for Fast Transfer Hydrogenation of Carbonyl Compounds in 2-Propanol”, Eur. J. Inorg. Chem., 2008, 4041-4053.
  • [ 21] Cavallo, M., Arnodo, D., Mannu, A., Blangetti, M., Prandi, C., Baratta, W., 2021, “Salvatore Baldino Deep eutectic solvents as H2-sources for Ru(II)-catalyzed transfer hydrogenation of carbonyl compounds under mild conditions”, Tetrahedron 83, 131997
  • [ 22] Breuer, M., Ditrich, K., Habicher, T., Hauer, B., Kebeler, M., Sturmer, R., Zelinski, T., 2004, “Industrial methods for the production of optically active intermediates”, Angew. Chem., Int. Ed. 43, 788–824.
  • [ 23] Foubelo, F., Najera, C., Yus M., 2015, “Catalytic asymmetric transfer hydrogenation of ketones: recent advances”, Tetrahedron: Asymmetry, 26, 769–790
  • [ 24] Blanco, C. O., Llovera, L., Herrera, A., Dorta, R., Agrifoglio, G., Venuti, D., Landaeta, V. R., Pastr´an J., 2021, “Ruthenium (II) complexes with C2- and C1-symmetric bis-(+)-camphopyrazole ligands and their evaluation in catalytic transfer hydrogenation of aldehydes”, Inorganica Chimica Acta, 524, 120429.
  • [ 25] Ak, B., Elma, D., Meriç, N., Kayan, C., Işık, U., Aydemir, M., Durap, F., Baysal, A., 2013, “New chiral ruthenium(II)–phosphinite complexes containing a ferrocenyl group in enantioselective transfer hydrogenations of aromatic ketones”, Tetrahedron:Asymmetry, 24, 1257-1264.
  • [26 ] Ak, B., Aydemir, M., Ocak, Y. S., Durap, F., Kayan, C., Baysal, A., Temel, H., 2014, “Readily available ferrocenyl-phosphinite ligands for Ru(II)-catalyzed enantioselective transfer hydrogenation of ketones and fabrication of hybrid heterojunctions”, Inorg. Chim. Acta, 409, 244-253.
  • [27 ] Aydemir, M., Baysal, A., Meric, N., Gümgüm, B., 2009, “New active ruthenium(II) complexes based N3,N3’-bis(diphenylphosphino)-2,20-bipyridine-3,3’-diamine and P,P’-diphenylphosphinous acid-P,P’-[2,2’-bipyridine]-3,3’-diyl ester ligands for transfer of aromatic ketones by propan-2-ol”, J. Organomet. Chem., 694, 2488-2492.
  • [28 ] Elma, D., Durap, F., Aydemir, M., Baysal, A., Meriç, N., Ak, B., Turgut, Y., Gümgüm, B., 2013, “Screening of C2-symmetric chiral phosphinites as ligands for ruthenium(II)-catalyzed asymmetric transfer hydrogenation of prochiral aromatic ketones”, J. Organomet. Chem., 729, 46-52.
  • [29 ] Aydemir, M., Meric, N., Baysal, A., Gümgüm, B., Toğrul, M., Turgut, Y., 2010, “A modular design of ruthenium(II) catalysts with chiral C2-symmetric phosphinite ligands for effective asymmetric transfer hydrogenation of aromatic ketones”, Tetrahedron: Asymmetry, 21, 703-710.
  • [ 30] Aydemir, M., Meric, N., Baysal, A., Kayan, C., Toğrul, M., Gümgüm, B., 2010, “New chiral phosphinite ligands with C2-symmetric axis and their possible applications in Ru-catalyzed asymmetric transfer hydrogenation”, Appl. Organomet. Chem., 24, 215-221.
  • [31 ] Aydemir, M., Meric, N., Durap, F., Baysal, A., Toğrul, M., 2010, “Asymmetric transfer hydrogenation of aromatic ketones with the ruthenium(II) catalyst derived from C2 symmetric N,N0-bis[(1S)-1-benzyl-2-O-(diphenylphosphinite)ethyl]ethanediamide”, J. Organomet. Chem., 695, 1392-1398.
  • [ 32] Aydemir, M., Durap, F., Baysal, A., Meric, N., Buldağ, A., Gümgüm, B., Özkar, S., Yıldırım, L. T., 2010, “Novel neutral phosphinite bridged dinuclear ruthenium(II) arene complexes and their catalytic use in transfer hydrogenation of aromatic ketones: X-ray structure of a new Schiff base, N3,N3-di-2-hydroxybenzylidene-[2,2]bipyridinyl-3,3-diamine”, J. Mol. Catal A: Chemical, 326, 75-81.
  • [ 33] Holbrey, J. D., Turner, M. B., Reichert W. M., and Rogers ‘R. D., 2003, “New ionic liquids containing an appended hydroxyl functionality from the atom-efficient, one-pot reaction of 1-methylimidazole and acid with propylene oxide”, Green Chem., 5, 731–736.
  • [ 34] Glas H., and Thiel, W. R., 1998, “Microwave assisted synthesis of chiral imidazolyl and pyrazolyl alcohols”, Tetrahedron Letters, 39, 5509-5510
  • [35 ] Glas, H., Herdtweck, E., Spiegler, M., Pleier, A., Thiel W. R., 2001, “A simple access to palladium complexes of functionalized heterocyclic carbenes”, Journal of Organometallic Chemistry, 626, 100–105.
  • [ 36] Paul C. E., Lavandera I., Gotor-Ferna´ndez V., Gotor V., 2014, “Imidazolium-Based Ionic Liquids as Non-conventional Media for Alcohol Dehydrogenase-Catalysed Reactions”, Top Catal., 57,332–338.
  • [ 37] Arnold, P. L., Scarisbrick, A. C., Blake A. J., Wilson C., 2001, “Chelating alkoxy-N-heterocyclic carbene complexes of silver and copper”, Chem. Commun., 2340–2341.
  • [ 38] Allegue, A., Albert-Soriano, M., Pastor, I. M., 2015, “A comparative study of hydroxyl- and carboxylate-functionalized imidazolium and benzimidazolium salts as precursors for N-heterocyclic carbene ligands”, Appl. Organometal. Chem., 29, 624–632.
  • [ 39] Chen, C., 2010, “A functionalised ionic liquid: 1-(3-chloro-2- hydroxypropyl)-3-methyl imidazolium chloride”, Phy Chem Liq, 48, 298–306
  • [40 ] Arslan, N., 2020, “Enantioselective transfer hydrogenation of pro-chiral ketones catalyzed by novel ruthenium and iridium complexes of well-designed phosphinite ligand”, Phosphorus, Sulfur, and Silicon and The Related Elements, Vol. 195, NO. 8, 628–637.
  • [ 41] Rafikova, K., Ertekin Binbay, N., Meriç, N., Kerimkulova, A., Zazybin, A., Binbay, V., Okumuş, V., Kayan, C., Işik, U., Arslan, N., Aydemir, M., 2020, “Biological assays and theoretical density functional theory calculations of Rh(I), Ir(III), and Ru(II) complexes of chiral phosphinite ligand”, Applied Organometallic Chemistry, 34, 5658.
  • [42 ] Meriç, N., Kayan, C., Rafikova, K., Zazybin, A., Okumuş, V., Aydemir, M., Durap, F., 2019, “Synthesis of ionic liquid-based Ru(II)-phosphinite complexes and evaluation of their antioxidant, antibacterial, DNA-binding, and DNA cleavage activities”, Chemical Papers, 73, 1199-1208.
  • [43 ] Meriç, N., Aydemir, M., Işık, U., Ocak, Y. S., Rafikova, K., Pasa, S., Kayan, C., Durap, F., Zazybin, A., Temel, H., 2014, “Cross-coupling reactions in water using ionic liquid-based palladium(II)–phosphinite complexes as outstanding catalysts”, Applied Organometallic Chemistry, 28, 818–825.
  • [44 ] Aydemir, M., Meriç, N., Baysal, A., Turgut, Y., Kayan, C., Şeker, S., Toğrul, M., Gümgüm, B., 2011, “Asymmetric transfer hydrogenation of acetophenone derivatives with novel chiral phosphinite based η6-p-cymene/ruthenium(II) catalysts”, Journal of Organometallic Chemistry 696, 1541-1546.
  • [45 ] Ruhlan, K., Gigler, P., Herdweck, E., 2008, “Some phosphinite complexes of Rh and Ir, their intramolecular reactivity and DFT calculations about their application in biphenyl metathesis”, J. Organomet. Chem., 693, 874-893.
  • [46 ] Broger, E.A., Burkart, W., Hennig, M., Scalone, M., Schmid, R., 1998, “Some phosphinite complexes of Rh and Ir, their intramolecular reactivity and DFT calculations about their application in biphenyl metathesis” Tetrahedron:Asymmetry 9, 4043-4054.
  • [ 47] Roucoux, A., Thieffry, L., Carpentier, J., Devocelle, M., Méliet, C., Agbossou, F., Mortreux, A., Welch, A. J., 1996, “Amidophosphine−Phosphinites:  Synthesis and Use in Rhodium-Based Asymmetric Hydrogenation of Activated Keto Compounds. Crystal Structure of Bis[(μ-chloro)((S)-2-((diphenylphosphino)oxy)-2-phenyl- N-(diphenylphosphino)-N-methylacetamide)rhodium(I)]”, Organometallics, 15, 10, 2440–2449.
  • [ 48] Meric, N., 2012, “Heterodonör Ligand Sentez ve Katalitik Uygulamalarinin Araştırılması”, Doktora Tezi, Dicle Üniversitesi Fen Bilimleri Enstitüsü, Diyarbakır, Türkiye.
  • [49 ] Bozec, H. Le, Touchard, D., Dixneuf, P. H., 1989, “Organometallic Chemistry of Arene Ruthenium and Osmium Complexes” Adv. Organomet. Chem., 29, 163-247.
  • [ 50] Zassinowich, G., Mestroni, G., Gladiali, S., 1992, “Asymmetric hydrogen transfer reactions promoted by homogeneous transition metal catalysts”, Chem. Rev., 92, 1051-1069.
  • [51 ] Palmer, M. J., Wills, M., 1999, “Asymmetric transfer hydrogenation of C=O and C=N bonds”, Tetrahedron: Asymmetry, 10, 2045-2061.
  • [ 52] Chaudret, B. N., Cole-Hamilton, D. J., Nohr, R. S., Wilkinson, G., 1977, “The reactions of chlorohydrido- and dichloro-tris(triphenylphosphine) ruthenium(II) with alkali hydroxides and alkoxides. Hydridohydroxobis(triphenylphosphine)ruthenium(II) monosolvates, their reactions and related compounds”, J. Chem. Soc., Dalton Trans., 1546-1557
  • [53 ] Vaska, L., Diluzio, J. W., 1962, “On the Origin of Hydrogen in Metal Hydride Complexes Formed by Reaction With Alcohols”, J. Am. Chem. Soc., 84, 4989-4990.
  • [ 54] Mannu, A., Grabulosa A., Baldino S., 2020, “Transfer Hydrogenation from 2-propanol to Acetophenone Catalyzed by [RuCl2(η 6 -arene)P] (P = monophosphine) and [Rh(PP)2]X (PP = diphosphine, X = Cl−, BF4 −) Complexes”, Catalysts, 10, 162; doi:10.3390/catal10020162.
  • [55 ] Meriç, N., Durap, F., Aydemir, M., Baysal, A., 2014, “The application of tunable tridendate P-based ligands for the Ru(II)-catalysed transfer hydrogenation of various ketones”, Applied Organometallic Chemistry, 28, 803–808.
  • [56 ] Kayan, C., Meriç, N., Rafikova, K., Zazybin, A., Gürbüz, N., Karakaplan, M., Aydemir, M., 2018, “A new class of well-defined ruthenium catalysts for enantioselective transfer hydrogenation of various ketones” Journal of Organometallic Chemistry, 869, 37-47.
  • [ 57] Meriç, N., Kayan, C., Gürbüz, N., Karakaplan, M., Erkin Binbay, N., Aydemir, M., 2017, "New functional chiral P-based ligands and application in ruthenium-catalyzed enantioselective transfer hydrogenation of ketones", Tetrahedron: Asymmetry 28, 1739-1749.
  • [58 ] Ak, B., Aydemir, M., Durap, F., Meriç, N., Elma, D., Baysal, A., 2015, “Highly efficient iridium catalysts based on C2-symmetric ferrocenyl phosphinite ligands for asymmetric transfer hydrogenations of aromatic ketones”, Tetrahedron: Asymmetry, 26, 1307-1313.
  • [ 59] Tyagi, N., Borah, G., Patel P., Ramaiah, D., 2021, “Recent Advances in Ru Catalyzed Transfer Hydrogenation and Its Future Perspectives”, doi: 10.5772/intechopen.96464
  • [ 60] Faller, J. W., Lavoie, A. R., 2001, “Catalysts for the Asymmetric Transfer Hydrogenation of Ketones Derived from l-Prolinamide and (p-CymeneRuCl2)2 or (Cp*RhCl2)2”, Organometallics, 20, 5245-5247.
  • [61 ] Özdemir, I., Yaşar, S., Çetinkaya, B., 2005, “Ruthenium(II) N-heterocyclic Carbene Complexes in the Transfer Hydrogenation of Ketones”, Trans. Met. Chem., 30, 831-835.
  • [62 ] Ak, B., Aydemir, M., Durap, F., Meriç, N., Baysal, A., 2015, “The first application of C2-symmetric ferrocenyl phosphinite ligands for rhodium-catalyzed asymmetric transfer hydrogenation of various ketones”, Inorganica Chimica Acta, 438, 42–51.
Yıl 2022, Cilt: 8 Sayı: 1, 1 - 15, 17.06.2022
https://doi.org/10.51477/mejs.1077805

Öz

Proje Numarası

FEN.20.001

Kaynakça

  • [ 1] Chauvin, R. 2000. “Zwitterionic Organometallates", Eur. J. Inorg. Chem., 4, 577–591.
  • [ 2] Zhang, H., Li, Y.-Q., Wang, P., Lu, Y., Zhao, X.-L., Liu, Y. 2016. “Effect of positive-charges in diphosphino- imidazolium salts on thestructures of Ir-complexes and catalysis for hydroformylation", Journal of Molecular Catalysis A: Chemical, 411, 337–343.
  • [3 ] Li, Y.Q., Wang, P., Zhang, H., Zhao, X.L., Lu, Y., Popovi´c, Z., Liu, Y. 2015. “Influence of electrostatic repulsive force and electron-withdrawing effect in ionic diphosphine on regioselectivity of rhodium-catalyzed hydroformylation of 1-octene", J. Mol. Catal. A: Chem., 402, 37–45.
  • [ 4] You, H.X., Wang, Y.Y., Zhao, X.L., Chen, S.J., Liu, Y. 2013. “Stable Ionic Rh(I,II,III) Complexes Ligated by an Imidazolium-Substituted Phosphine with π-Acceptor Character: Synthesis, Characterization, and Application to Hydroformylation", Organometallics, 32(9),, 2698–2704.
  • [5 ] Zhang, J., Wang, Y.Y., Zhao, X.L., Liu, Y. 2014. “Phosphane‐Ligated Ionic Palladium Complexes: Synthesis, Characterization and Application as Efficient and Reusable Precatalysts for the Homogeneous Carbonylative Sonogashira Reaction under CuI‐Free Conditions", Eur. J. Inorg. Chem., 2014 (6), 975–985.
  • [6 ] Zhou, C.L., Zhang, J., Ðakovic, M., Popovic, Z., Zhao, X.L., Liu, Y. 2012. “Synthesis of an Ionic Paramagnetic Ruthenium (III) Complex and Its Application as an Efficient and Recyclable Catalyst for the Transfer Hydrogenation of Ketones", Eur. J. Inorg. Chem., 2012 (21), 3435–3440.
  • [ 7] Luska, K.L., Demmans, K.Z., Stratton, S.A., Moores, A. 2012. “Rhodium complexes stabilized by phosphine-functionalized phosphonium ionic liquids used as higher alkene hydroformylation catalysts: influence of the phosphonium headgroup on catalytic activity", Dalton Trans., 41, 13533–13540.
  • [8 ] Canac, Y., Maaliki, C., Abdellahab, I., Chauvin, R. 2012. “Carbeniophosphanes and their carbon → phosphorus → metal ternary complexes", New J. Chem., 36, 17–27.
  • [ 9] Valizadeh, H., Khalili, E. 2012. “Efficient synthesis of symmetrical phthalate and maleate diesters using phosphinite ionic liquids", Iran Chem Soc., 9, 529–534.
  • [10 ] Valizadeh, H., Shockravi, A. 2009 (a). “Imidazolium-Based Phosphinite Ionic Liquid as Reusable Catalyst and Solvent for One- Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-(thio)ones", Heteroatom Chemistry, 20(5), 284-288.
  • [11 ] Valizadeh, H., Shockravi, A. 2009 (b). “Task-Specific Ionic Liquid as Reagent and Reaction Medium for the One-Pot Horner–Wadsworth–Emmons–Type Reaction Under Microwave Irradiation", Synthetic Communications1, 39, 4341–4349.
  • [ 12] Valizadeh, H., Gholipour, H. 2010. “Imidazolium-Based Phosphinite Ionic Liquid (ILOPPh2) as Reusable Catalyst and Solvent for the Knoevenagel Condensation Reaction", Synthetic Communications1, 40, 1477–1485.
  • [ 13] Iranpoor, N. Firouzabadi, H., Azadi, R. 2008. “Imidazolium-based phosphinite ionic liquid (IL-OPPh2) as Pd ligand and solvent for selective dehalogenation or homocoupling of aryl halides", Journal of Organometallic Chemistry, 693, 2469–2472.
  • [ 14] Iranpoor, N. Firouzabadi, H., Azadi, R. 2010. “Diphenylphosphinite ionic liquid (IL-OPPh2): A solvent and ligand for palladium-catalyzed silylation and dehalogenation reaction of aryl halides with triethylsilane", Journal of Organometallic Chemistry, 695, 887–890.
  • [15 ] Iranpoor, N. Firouzabadi, H., Azadi, R. 2007. “An Imidazolium-Based Phosphinite Ionic Liquid (IL-OPPh2) as a Reusable Reaction Medium and PdII Ligand in Heck Reactions of Aryl Halides with Styrene and n-Butyl Acrylate", Eur. J. Org. Chem., 2197–2201.
  • [ 16] Aydemir, M., Rafikova, K., Kystaubayeva, N., Pasa, S., Meriç, N., Ocak, Y. S., Zazybin, A., Temel, H., Gürbüz, N., Özdemir, İ., 2014, “Ionic liquid based Ru(II)–phosphinite compounds and their catalytic use in transfer hydrogenation: X-ray structure of an ionic compound 1-chloro-3-(3-methylimidazolidin-1-yl)propan-2-ol”, Polyhedron, 81, 245–255.
  • [17 ] Elma Karakaş, D., Durap, F., Baysal, A., Ocak, Y. S., Rafikova, K., Çavus Kaya, E., Zazybin, A., Temel, H., Kayan, C., Meriç, N., Aydemir, M., 2016, “Transfer hydrogenation reaction using novel ionic liquid based Rh(I) and Ir(III)-phosphinite complexes as catalyst,” Journal of Organometallic Chemistry, 824, 25-32.
  • [18 ] Meriç, N., Arslan, N., Kayan, C., Rafikova, K., Zazybin, A., Kerimkulova, A., Aydemir, M., 2019, “Catalysts for the asymmetric transfer hydrogenation of various ketones from [3-[(2S)-2-[(diphenylphosphanyl)oxy]-3-phenoxypropyl]-1-methyl-1H-imidazol-3-ium chloride] and [Ru(eta(6)-arene)(mu-Cl)Cl](2), Ir(eta(5)-C5Me5)(mu-Cl)Cl](2) or [Rh(mu-Cl)(cod)](2)”, Inorganica Chimica Acta, 492, 108-118.
  • [19 ] Ojima, I., 2010, Catalytic Asymmetric Synthesis, John Wiley, Hoboken, N.J., ISBN: 978-0-470-17577-4
  • [20 ] Baratta, W., Rigo, P., 2008, “1-(Pyridin-2-yl)methanamine-Based Ruthenium Catalysts for Fast Transfer Hydrogenation of Carbonyl Compounds in 2-Propanol”, Eur. J. Inorg. Chem., 2008, 4041-4053.
  • [ 21] Cavallo, M., Arnodo, D., Mannu, A., Blangetti, M., Prandi, C., Baratta, W., 2021, “Salvatore Baldino Deep eutectic solvents as H2-sources for Ru(II)-catalyzed transfer hydrogenation of carbonyl compounds under mild conditions”, Tetrahedron 83, 131997
  • [ 22] Breuer, M., Ditrich, K., Habicher, T., Hauer, B., Kebeler, M., Sturmer, R., Zelinski, T., 2004, “Industrial methods for the production of optically active intermediates”, Angew. Chem., Int. Ed. 43, 788–824.
  • [ 23] Foubelo, F., Najera, C., Yus M., 2015, “Catalytic asymmetric transfer hydrogenation of ketones: recent advances”, Tetrahedron: Asymmetry, 26, 769–790
  • [ 24] Blanco, C. O., Llovera, L., Herrera, A., Dorta, R., Agrifoglio, G., Venuti, D., Landaeta, V. R., Pastr´an J., 2021, “Ruthenium (II) complexes with C2- and C1-symmetric bis-(+)-camphopyrazole ligands and their evaluation in catalytic transfer hydrogenation of aldehydes”, Inorganica Chimica Acta, 524, 120429.
  • [ 25] Ak, B., Elma, D., Meriç, N., Kayan, C., Işık, U., Aydemir, M., Durap, F., Baysal, A., 2013, “New chiral ruthenium(II)–phosphinite complexes containing a ferrocenyl group in enantioselective transfer hydrogenations of aromatic ketones”, Tetrahedron:Asymmetry, 24, 1257-1264.
  • [26 ] Ak, B., Aydemir, M., Ocak, Y. S., Durap, F., Kayan, C., Baysal, A., Temel, H., 2014, “Readily available ferrocenyl-phosphinite ligands for Ru(II)-catalyzed enantioselective transfer hydrogenation of ketones and fabrication of hybrid heterojunctions”, Inorg. Chim. Acta, 409, 244-253.
  • [27 ] Aydemir, M., Baysal, A., Meric, N., Gümgüm, B., 2009, “New active ruthenium(II) complexes based N3,N3’-bis(diphenylphosphino)-2,20-bipyridine-3,3’-diamine and P,P’-diphenylphosphinous acid-P,P’-[2,2’-bipyridine]-3,3’-diyl ester ligands for transfer of aromatic ketones by propan-2-ol”, J. Organomet. Chem., 694, 2488-2492.
  • [28 ] Elma, D., Durap, F., Aydemir, M., Baysal, A., Meriç, N., Ak, B., Turgut, Y., Gümgüm, B., 2013, “Screening of C2-symmetric chiral phosphinites as ligands for ruthenium(II)-catalyzed asymmetric transfer hydrogenation of prochiral aromatic ketones”, J. Organomet. Chem., 729, 46-52.
  • [29 ] Aydemir, M., Meric, N., Baysal, A., Gümgüm, B., Toğrul, M., Turgut, Y., 2010, “A modular design of ruthenium(II) catalysts with chiral C2-symmetric phosphinite ligands for effective asymmetric transfer hydrogenation of aromatic ketones”, Tetrahedron: Asymmetry, 21, 703-710.
  • [ 30] Aydemir, M., Meric, N., Baysal, A., Kayan, C., Toğrul, M., Gümgüm, B., 2010, “New chiral phosphinite ligands with C2-symmetric axis and their possible applications in Ru-catalyzed asymmetric transfer hydrogenation”, Appl. Organomet. Chem., 24, 215-221.
  • [31 ] Aydemir, M., Meric, N., Durap, F., Baysal, A., Toğrul, M., 2010, “Asymmetric transfer hydrogenation of aromatic ketones with the ruthenium(II) catalyst derived from C2 symmetric N,N0-bis[(1S)-1-benzyl-2-O-(diphenylphosphinite)ethyl]ethanediamide”, J. Organomet. Chem., 695, 1392-1398.
  • [ 32] Aydemir, M., Durap, F., Baysal, A., Meric, N., Buldağ, A., Gümgüm, B., Özkar, S., Yıldırım, L. T., 2010, “Novel neutral phosphinite bridged dinuclear ruthenium(II) arene complexes and their catalytic use in transfer hydrogenation of aromatic ketones: X-ray structure of a new Schiff base, N3,N3-di-2-hydroxybenzylidene-[2,2]bipyridinyl-3,3-diamine”, J. Mol. Catal A: Chemical, 326, 75-81.
  • [ 33] Holbrey, J. D., Turner, M. B., Reichert W. M., and Rogers ‘R. D., 2003, “New ionic liquids containing an appended hydroxyl functionality from the atom-efficient, one-pot reaction of 1-methylimidazole and acid with propylene oxide”, Green Chem., 5, 731–736.
  • [ 34] Glas H., and Thiel, W. R., 1998, “Microwave assisted synthesis of chiral imidazolyl and pyrazolyl alcohols”, Tetrahedron Letters, 39, 5509-5510
  • [35 ] Glas, H., Herdtweck, E., Spiegler, M., Pleier, A., Thiel W. R., 2001, “A simple access to palladium complexes of functionalized heterocyclic carbenes”, Journal of Organometallic Chemistry, 626, 100–105.
  • [ 36] Paul C. E., Lavandera I., Gotor-Ferna´ndez V., Gotor V., 2014, “Imidazolium-Based Ionic Liquids as Non-conventional Media for Alcohol Dehydrogenase-Catalysed Reactions”, Top Catal., 57,332–338.
  • [ 37] Arnold, P. L., Scarisbrick, A. C., Blake A. J., Wilson C., 2001, “Chelating alkoxy-N-heterocyclic carbene complexes of silver and copper”, Chem. Commun., 2340–2341.
  • [ 38] Allegue, A., Albert-Soriano, M., Pastor, I. M., 2015, “A comparative study of hydroxyl- and carboxylate-functionalized imidazolium and benzimidazolium salts as precursors for N-heterocyclic carbene ligands”, Appl. Organometal. Chem., 29, 624–632.
  • [ 39] Chen, C., 2010, “A functionalised ionic liquid: 1-(3-chloro-2- hydroxypropyl)-3-methyl imidazolium chloride”, Phy Chem Liq, 48, 298–306
  • [40 ] Arslan, N., 2020, “Enantioselective transfer hydrogenation of pro-chiral ketones catalyzed by novel ruthenium and iridium complexes of well-designed phosphinite ligand”, Phosphorus, Sulfur, and Silicon and The Related Elements, Vol. 195, NO. 8, 628–637.
  • [ 41] Rafikova, K., Ertekin Binbay, N., Meriç, N., Kerimkulova, A., Zazybin, A., Binbay, V., Okumuş, V., Kayan, C., Işik, U., Arslan, N., Aydemir, M., 2020, “Biological assays and theoretical density functional theory calculations of Rh(I), Ir(III), and Ru(II) complexes of chiral phosphinite ligand”, Applied Organometallic Chemistry, 34, 5658.
  • [42 ] Meriç, N., Kayan, C., Rafikova, K., Zazybin, A., Okumuş, V., Aydemir, M., Durap, F., 2019, “Synthesis of ionic liquid-based Ru(II)-phosphinite complexes and evaluation of their antioxidant, antibacterial, DNA-binding, and DNA cleavage activities”, Chemical Papers, 73, 1199-1208.
  • [43 ] Meriç, N., Aydemir, M., Işık, U., Ocak, Y. S., Rafikova, K., Pasa, S., Kayan, C., Durap, F., Zazybin, A., Temel, H., 2014, “Cross-coupling reactions in water using ionic liquid-based palladium(II)–phosphinite complexes as outstanding catalysts”, Applied Organometallic Chemistry, 28, 818–825.
  • [44 ] Aydemir, M., Meriç, N., Baysal, A., Turgut, Y., Kayan, C., Şeker, S., Toğrul, M., Gümgüm, B., 2011, “Asymmetric transfer hydrogenation of acetophenone derivatives with novel chiral phosphinite based η6-p-cymene/ruthenium(II) catalysts”, Journal of Organometallic Chemistry 696, 1541-1546.
  • [45 ] Ruhlan, K., Gigler, P., Herdweck, E., 2008, “Some phosphinite complexes of Rh and Ir, their intramolecular reactivity and DFT calculations about their application in biphenyl metathesis”, J. Organomet. Chem., 693, 874-893.
  • [46 ] Broger, E.A., Burkart, W., Hennig, M., Scalone, M., Schmid, R., 1998, “Some phosphinite complexes of Rh and Ir, their intramolecular reactivity and DFT calculations about their application in biphenyl metathesis” Tetrahedron:Asymmetry 9, 4043-4054.
  • [ 47] Roucoux, A., Thieffry, L., Carpentier, J., Devocelle, M., Méliet, C., Agbossou, F., Mortreux, A., Welch, A. J., 1996, “Amidophosphine−Phosphinites:  Synthesis and Use in Rhodium-Based Asymmetric Hydrogenation of Activated Keto Compounds. Crystal Structure of Bis[(μ-chloro)((S)-2-((diphenylphosphino)oxy)-2-phenyl- N-(diphenylphosphino)-N-methylacetamide)rhodium(I)]”, Organometallics, 15, 10, 2440–2449.
  • [ 48] Meric, N., 2012, “Heterodonör Ligand Sentez ve Katalitik Uygulamalarinin Araştırılması”, Doktora Tezi, Dicle Üniversitesi Fen Bilimleri Enstitüsü, Diyarbakır, Türkiye.
  • [49 ] Bozec, H. Le, Touchard, D., Dixneuf, P. H., 1989, “Organometallic Chemistry of Arene Ruthenium and Osmium Complexes” Adv. Organomet. Chem., 29, 163-247.
  • [ 50] Zassinowich, G., Mestroni, G., Gladiali, S., 1992, “Asymmetric hydrogen transfer reactions promoted by homogeneous transition metal catalysts”, Chem. Rev., 92, 1051-1069.
  • [51 ] Palmer, M. J., Wills, M., 1999, “Asymmetric transfer hydrogenation of C=O and C=N bonds”, Tetrahedron: Asymmetry, 10, 2045-2061.
  • [ 52] Chaudret, B. N., Cole-Hamilton, D. J., Nohr, R. S., Wilkinson, G., 1977, “The reactions of chlorohydrido- and dichloro-tris(triphenylphosphine) ruthenium(II) with alkali hydroxides and alkoxides. Hydridohydroxobis(triphenylphosphine)ruthenium(II) monosolvates, their reactions and related compounds”, J. Chem. Soc., Dalton Trans., 1546-1557
  • [53 ] Vaska, L., Diluzio, J. W., 1962, “On the Origin of Hydrogen in Metal Hydride Complexes Formed by Reaction With Alcohols”, J. Am. Chem. Soc., 84, 4989-4990.
  • [ 54] Mannu, A., Grabulosa A., Baldino S., 2020, “Transfer Hydrogenation from 2-propanol to Acetophenone Catalyzed by [RuCl2(η 6 -arene)P] (P = monophosphine) and [Rh(PP)2]X (PP = diphosphine, X = Cl−, BF4 −) Complexes”, Catalysts, 10, 162; doi:10.3390/catal10020162.
  • [55 ] Meriç, N., Durap, F., Aydemir, M., Baysal, A., 2014, “The application of tunable tridendate P-based ligands for the Ru(II)-catalysed transfer hydrogenation of various ketones”, Applied Organometallic Chemistry, 28, 803–808.
  • [56 ] Kayan, C., Meriç, N., Rafikova, K., Zazybin, A., Gürbüz, N., Karakaplan, M., Aydemir, M., 2018, “A new class of well-defined ruthenium catalysts for enantioselective transfer hydrogenation of various ketones” Journal of Organometallic Chemistry, 869, 37-47.
  • [ 57] Meriç, N., Kayan, C., Gürbüz, N., Karakaplan, M., Erkin Binbay, N., Aydemir, M., 2017, "New functional chiral P-based ligands and application in ruthenium-catalyzed enantioselective transfer hydrogenation of ketones", Tetrahedron: Asymmetry 28, 1739-1749.
  • [58 ] Ak, B., Aydemir, M., Durap, F., Meriç, N., Elma, D., Baysal, A., 2015, “Highly efficient iridium catalysts based on C2-symmetric ferrocenyl phosphinite ligands for asymmetric transfer hydrogenations of aromatic ketones”, Tetrahedron: Asymmetry, 26, 1307-1313.
  • [ 59] Tyagi, N., Borah, G., Patel P., Ramaiah, D., 2021, “Recent Advances in Ru Catalyzed Transfer Hydrogenation and Its Future Perspectives”, doi: 10.5772/intechopen.96464
  • [ 60] Faller, J. W., Lavoie, A. R., 2001, “Catalysts for the Asymmetric Transfer Hydrogenation of Ketones Derived from l-Prolinamide and (p-CymeneRuCl2)2 or (Cp*RhCl2)2”, Organometallics, 20, 5245-5247.
  • [61 ] Özdemir, I., Yaşar, S., Çetinkaya, B., 2005, “Ruthenium(II) N-heterocyclic Carbene Complexes in the Transfer Hydrogenation of Ketones”, Trans. Met. Chem., 30, 831-835.
  • [62 ] Ak, B., Aydemir, M., Durap, F., Meriç, N., Baysal, A., 2015, “The first application of C2-symmetric ferrocenyl phosphinite ligands for rhodium-catalyzed asymmetric transfer hydrogenation of various ketones”, Inorganica Chimica Acta, 438, 42–51.
Toplam 62 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Doğrusal Olmayan Optik ve Spektroskopi, İnorganik Kimya
Bölüm Makale
Yazarlar

Uğur Işık 0000-0003-1010-9563

Nermin Meriç Bu kişi benim 0000-0003-0456-5124

Murat Aydemir 0000-0002-4238-5012

Proje Numarası FEN.20.001
Yayımlanma Tarihi 17 Haziran 2022
Gönderilme Tarihi 23 Şubat 2022
Kabul Tarihi 5 Nisan 2022
Yayımlandığı Sayı Yıl 2022 Cilt: 8 Sayı: 1

Kaynak Göster

IEEE U. Işık, N. Meriç, ve M. Aydemir, “NOVEL MONONUCLEAR METAL-PHOSPHINITE COMPOUNDS AND CATALYTIC PERFORMANCE IN TRANSFER HYDROGENATION OF KETONES”, MEJS, c. 8, sy. 1, ss. 1–15, 2022, doi: 10.51477/mejs.1077805.

Creative Commons License

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License

TRDizinlogo_live-e1586763957746.png   ici2.png     scholar_logo_64dp.png    CenterLogo.png     crossref-logo-landscape-200.png  logo.png         logo1.jpg   DRJI_Logo.jpg  17826265674769  logo.png