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Issue 7, 2018
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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

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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. The reaction of the imidazolium 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 (1.55 mg ml−1), sulfonated N-alkyl substituted NHC complexes display good solubility in water (up to 400 mg mL−1). All complexes were examined as catalysts in the transfer hydrogenation of acetophenone, which is quantitatively and highly selective reduced to 1-phenylethanol and 1-cyclohexylethanol. 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.

Graphical abstract: 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

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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., 2018,47, 2318-2329
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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. Bayón Castañón, M. Kaposi, R. M. Reich and F. E. Kühn, Dalton Trans., 2018, 47, 2318
    DOI: 10.1039/C7DT04684G

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