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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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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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