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

Year 2022, , 1 - 15, 17.06.2022
https://doi.org/10.51477/mejs.1077805

Abstract

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.

Supporting Institution

Dicle University Research Fund

Project Number

FEN.20.001

Thanks

Dicle University Research Fund

References

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Year 2022, , 1 - 15, 17.06.2022
https://doi.org/10.51477/mejs.1077805

Abstract

Project Number

FEN.20.001

References

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  • [ 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
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  • [ 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.
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Details

Primary Language English
Subjects Nonlinear Optics and Spectroscopy, Inorganic Chemistry
Journal Section Article
Authors

Uğur Işık 0000-0003-1010-9563

Nermin Meriç This is me 0000-0003-0456-5124

Murat Aydemir 0000-0002-4238-5012

Project Number FEN.20.001
Publication Date June 17, 2022
Submission Date February 23, 2022
Acceptance Date April 5, 2022
Published in Issue Year 2022

Cite

IEEE U. Işık, N. Meriç, and M. Aydemir, “NOVEL MONONUCLEAR METAL-PHOSPHINITE COMPOUNDS AND CATALYTIC PERFORMANCE IN TRANSFER HYDROGENATION OF KETONES”, MEJS, vol. 8, no. 1, pp. 1–15, 2022, doi: 10.51477/mejs.1077805.

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