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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

1,2
, 3,4,* , 3
, 5
, 6
, 7
, 8
, 9
, 5
, 10
 and 5,*
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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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