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Water-soluble transition metal complexes of Ruthenium(II), Osmium(II), Rhodium (III) and Iridium (III) with chelating N-heterocyclic carbene ligands in hydrogenation and transfer hydrogenation catalysis

Abstract

The synthesis of novel Ru(II), Os(II), Rh(III) and Ir(III) mono N-heterocyclic carbene (NHC) complexes with a pyridine substituent is reported. Reaction of the imidalozium salts bearing N-alkyl and sulfonated N-alkyl substituents with Ag2O leads to the formation of the corresponding Ag(I) complexes. The metal complexes are available in good yields via transmetallation reactions from the corresponding silver complexes and [ArMCl2]2, where Ar = p-cymene or Cp* and M = Ru, Os, Rh or Ir. While N-alkyl substituted NHC complexes are almost insoluble in water (1.55mg/ml), sulfonated N-alkyl substituted NHC complexes display good solubility in water (up to 400 mg/mL). All complexes were examined as catalysts in transfer hydrogenation of acetophenone, which is quantitatively and highly selective reduced to 1-phenylethanol and 1-cyclohexyl ethanol. Additionally, the water-soluble complexes were examined in the complete hydrogenation of acetophenone with hydrogen in an autoclave, showing high conversions compared to literature-known systems.

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Publication details

The article was received on 11 Dec 2017, accepted on 10 Jan 2018 and first published on 11 Jan 2018


Article type: Paper
DOI: 10.1039/C7DT04684G
Citation: Dalton Trans., 2018, Accepted Manuscript
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    Water-soluble transition metal complexes of Ruthenium(II), Osmium(II), Rhodium (III) and Iridium (III) with chelating N-heterocyclic carbene ligands in hydrogenation and transfer hydrogenation catalysis

    E. Bayon Castanon, M. Kaposi, R. M. Reich and F. E. Kühn, Dalton Trans., 2018, Accepted Manuscript , DOI: 10.1039/C7DT04684G

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