Hydrogenation and hydrogenolysis of furfural and furfuryl alcohol catalyzed by ruthenium(II) bis(diimine) complexes

Anitha S. Gowda, Sean Parkin, Folami T. Ladipo

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63 Scopus citations


The catalytic activity of ruthenium(II) bis(diimine) complexes cis-[Ru(6,6′-Cl 2bpy) 2(OH 2) 2](Z) 2 (1, Z = CF 3SO 3; 2, Z = (3,5-(CF 3) 2C 6H 3) 4B, i.e. BArF) and cis-[Ru(4,4′-Cl 2bpy) 2(OH 2) 2](Z) 2 (3, Z = CF 3SO 3; 4, Z = BArF) for the hydrogenation and/or the hydrogenolysis of furfural (FFR) and furfuryl alcohol (FFA) was investigated. The molecular structures of cis-[Ru(4,4′- Cl 2bpy) 2(CH 3CN) 2](CF 3SO 3) 2 (3′) and dimeric cis-[(Ru(4,4′-Cl 2bpy) 2Cl) 2](BArF) 2 (5) were characterized by X-ray crystallography. The structures are consistent with the anticipated reduction in steric hindrance about the ruthenium centers in comparison with corresponding complexes containing 6,6′-Cl 2bpy ligands. While compounds 1-4 are all active and highly selective catalysts for the hydrogenation of FFR to FFA under modest reaction conditions, 3 and 4 showed decreased activity. This is best explained in terms of reduced Lewis acidity of the Ru 2+ centers and reduced steric hindrance about the metal centers of catalysts 3 and 4. cis-[Ru(6,6′-Cl 2bpy) 2(OH 2) 2](BArF) 2 (2) also displayed high catalytic efficiency for the hydrogenation of FFA to tetrahydrofurfuryl alcohol. Presumably, this is because coordination of C=C bonds of FFA to the ruthenium center is poorly inhibited by non-coordinating BArF counterions. Interestingly, cis-[Ru(6,6′-Cl 2bpy) 2(OH 2) 2](CF 3SO 3) 2 (1) showed some catalytic activity in ethanol for the hydrogenolysis of FFA to 2-methylfuran, albeit with fairly modest selectivity. Nonetheless, these results indicate that ruthenium(II) bis(diimine) complexes need to be further explored as catalysts for the hydrogenolysis of C-O bonds of FFR, FFA, and related compounds.

Original languageEnglish
Pages (from-to)86-93
Number of pages8
JournalApplied Organometallic Chemistry
Issue number2
StatePublished - Feb 2012


  • carbon-oxygen bond hydrogenolysis
  • catalytic hydrogenation
  • furfuryl alcohol
  • ruthenium bis(diimine) complexes
  • tetrahydrofurfuryl alcohol

ASJC Scopus subject areas

  • Chemistry (all)
  • Inorganic Chemistry


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