A designed and potentially decadentate ligand for use in lanthanide(iii) catalysed biomass transformations: targeting diastereoselective trans-4,5-diaminocyclopentenone derivatives

Dalton Trans. 2020 Feb 21;49(7):2331-2336. doi: 10.1039/d0dt00183j. Epub 2020 Feb 5.

Abstract

The goal of this study was to design a ligand system which can accommodate single lanthanide(iii)-ions and investigate the properties of the resulting complexes. The complexes of all the accesible lanthanides and yttrium with the new ligand LH6 = N,N'-dimethyl-N,N'-ethylene-bis(5-bromo-3-(1H-benzimidazol-2-yl)hydrazineylidene)-2-hydroxybenzylamine) were obtained in high yield at room temperature under aerobic reaction conditions. The corresponding compounds were characterised using X-ray diffraction, FT-IR, elemental analysis and the optical properties of all complexes were investigated using UV-vis and fluorescence spectroscopy. The air stable complexes efficiently transform biomass furfural to trans-4,5-cyclopentenones in high yield.

MeSH terms

  • Biomass
  • Biotransformation
  • Catalysis
  • Coordination Complexes / chemical synthesis*
  • Coordination Complexes / chemistry
  • Crystallography, X-Ray
  • Cyclopentanes / chemistry
  • Cyclopentanes / metabolism*
  • Lanthanoid Series Elements / chemistry*
  • Ligands
  • Models, Molecular
  • Molecular Structure
  • Stereoisomerism

Substances

  • Coordination Complexes
  • Cyclopentanes
  • Lanthanoid Series Elements
  • Ligands