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

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2014 May 14

PMID 24818576

Authors

Hany W Darwish

Assem Barakat

Ayman Nafady

Mohammed Suleiman

Mousa Al-Noaimi

Belkheir Hammouti

Smaail Radi

Taibi Ben Hadda

Ahmad Abu-Obaid

Mohammad S Mubarak

Ismail Warad

Affiliations

Soon will be listed here.

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.

References

Song C, Lee S . Supported chiral catalysts on inorganic materials. Chem Rev. 2002; 102(10):3495-524. DOI: 10.1021/cr0103625. View

Warad I, Al-Othman Z, Al-Resayes S, Al-Deyab S, Kenawy E . Synthesis and characterization of novel inorganic-organic hybrid Ru(II) complexes and their application in selective hydrogenation. Molecules. 2010; 15(2):1028-40. PMC: 6263181. DOI: 10.3390/molecules15021028. View

Warad I, Al-Resayes S, Al-Othman Z, Al-Deyab S, Kenawy E . Synthesis and spectrosopic identification of hybrid 3-(triethoxysilyl)propylamine phosphine ruthenium(II) complexes. Molecules. 2010; 15(5):3618-33. PMC: 6263334. DOI: 10.3390/molecules15053618. View

Lu Z, Lindner E, Mayer H . Applications of sol-gel-processed interphase catalysts. Chem Rev. 2002; 102(10):3543-78. DOI: 10.1021/cr010358t. View

Warad I, Al-Noaimi M, Abdel-Rahman O, Awwadi F, Hammouti B, Hadda T . Trans/cis isomerization of [RuCl2{H2C=C(CH2PPh2)2)}(diamine)] complexes: synthesis, spectral, crystal structure and DFT calculations and catalytic activity in the hydrogenation of α,β-unsaturated ketones. Spectrochim Acta A Mol Biomol Spectrosc. 2013; 117:250-8. DOI: 10.1016/j.saa.2013.08.030. View

Abdur-Rashid K, Faatz M, Lough A, Morris R . Catalytic cycle for the asymmetric hydrogenation of prochiral ketones to chiral alcohols: direct hydride and proton transfer from chiral catalysts trans-Ru(H)(2)(diphosphine)(diamine) to ketones and direct addition of dihydrogen to the resulting.... J Am Chem Soc. 2001; 123(30):7473-4. DOI: 10.1021/ja015902u. View

Bergbreiter D . Using soluble polymers to recover catalysts and ligands. Chem Rev. 2002; 102(10):3345-84. DOI: 10.1021/cr010343v. View

Warad I . Supported and non-supported ruthenium(II)/phosphine/[3-(2-aminoethyl)aminopropyl]trimethoxysilane complexes and their activities in the chemoselective hydrogenation of trans-4-phenyl-3-butene-2-al. Molecules. 2010; 15(7):4652-69. PMC: 6257608. DOI: 10.3390/molecules15074652. View

Noyori R . Asymmetric catalysis: science and opportunities (Nobel lecture). Angew Chem Int Ed Engl. 2009; 41(12):2008-22. View

10.

Ohkuma T, Koizumi M, Muniz K, Hilt G, Kabuto C, Noyori R . trans-RuH(eta1-BH4)(binap)(1,2-diamine): a catalyst for asymmetric hydrogenation of simple ketones under base-free conditions. J Am Chem Soc. 2002; 124(23):6508-9. DOI: 10.1021/ja026136+. View

11.

Al-Noaimi M, Nafady A, Warad I, Alshwafy R, Husein A, Talib W . Heterotrimetallic Ru(II)/Pd(II)/Ru(II) complexes: synthesis, crystalstructure, spectral characterization, DFT calculation and antimicrobial study. Spectrochim Acta A Mol Biomol Spectrosc. 2013; 122:273-82. DOI: 10.1016/j.saa.2013.11.052. View