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Molecules 2014, 19(5), 5965-5980; doi:10.3390/molecules19055965
Article

Design, Synthesis, Characterization of Novel Ruthenium(II) Catalysts: Highly Efficient and Selective Hydrogenation of Cinnamaldehyde to (E)-3-Phenylprop-2-en-1-ol

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1 Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia 2 Department of Analytical Chemistry, Faculty of Pharmacy, Cairo University, Kasr El-Aini Street, ET 11562, Cairo, Egypt 3 Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia 4 Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, Alexandria 21321, Egypt 5 Department of Chemistry, Science College, An-Najah National University, P.O. Box 7, Nablus 0092, Palestine 6 Department of Chemistry, Hashemite University, Zarqa 13115, Jordan 7 LCAE-URAC18, Faculty of Science, University Mohammed Premier, Oujda-60000, Morocco 8 LCAE, Chemistry Department, Faculty of Sciences, University Mohammed Premier, Oujda-60000, Morocco 9 Lab of Chemical Material, FSO, University Mohammed Premier, Oujda-60000, Morocco 10 Department of Chemistry, The University of Jordan, Amman 11942, Jordan
* Authors to whom correspondence should be addressed.
Received: 1 April 2014 / Revised: 3 May 2014 / Accepted: 6 May 2014 / Published: 9 May 2014
(This article belongs to the Section Organic Synthesis)
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Abstract

In this contribution, two novel supported and non-supported ruthenium(II) complexes of type [RuCl2(dppme)(NN)] where [dppme is H2C=C(CH2PPh2)2 and NN is N1-(3-(trimethoxysilyl)propyl)ethane-1,2-diamine] were prepared. The NN co-ligand caused release of one of the dppme ligands from [RuCl2(dppme)2] precursor to yield complex 1. The process of substitution of dppme by NN was monitored by 31P{1H}-NMR. Taking advantage of the presence of trimethoxysilane group in the backbone of complex 1, polysiloxane xerogel counterpart, X1, was prepared via sol-gel immobilization using tetraethoxysilane as cross-linker. Both complexes 1 and X1 have been characterized via elemental analysis, CV and a number of spectroscopic techniques including FT-IR, 1H-, 13C-, and 31P-NMR, and mass spectrometry. Importantly, carbonyl selective hydrogenation was successfully accomplished under mild conditions using complex 1 as a homogenous catalyst and X1 as a heterogeneous catalyst, respectively.
Keywords: Ru(II) complexes; hydrogenation; diphosphine; cinnamic aldehyde; NMR Ru(II) complexes; hydrogenation; diphosphine; cinnamic aldehyde; NMR
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Darwish, H.W.; Barakat, A.; Nafady, A.; Suleiman, M.; Al-Noaimi, M.; Hammouti, B.; Radi, S.; Hadda, T.B.; Abu-Obaid, A.; Mubarak, M.S.; Warad, I. Design, Synthesis, Characterization of Novel Ruthenium(II) Catalysts: Highly Efficient and Selective Hydrogenation of Cinnamaldehyde to (E)-3-Phenylprop-2-en-1-ol. Molecules 2014, 19, 5965-5980.

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