Facile synthesis of nitrogen tetradentate ligands and their applications in Cu(I)-catalyzed N-arylation and azide-alkyne cycloaddition

Chemistry. 2009 Oct 12;15(40):10585-92. doi: 10.1002/chem.200901014.

Abstract

Five new tetradentate ligands [NNNN] with benzimidazolyl-imine or amine nitrogen donors have been synthesized in good yields under mild conditions from easily available substrates. trans-N,N'-bis(1-Ethyl-2-benzimidazolylmethylene)cyclohexane-1,2-diimine is the best accelerating ligand in this series that supports the Cu(I)-catalyzed Ullmann N-arylation and the direct three-component azide-alkyne cycloaddition reaction to give the corresponding substituted imidazole, pyrazole, and triazole in high yields. Single-crystal X-ray diffraction analysis of its complex with CuI reveals a novel one-dimensional coordination polymer of the metal chain bridged alternately by the [NNNN] ligand and diiodides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Azides / chemistry*
  • Catalysis
  • Copper / chemistry*
  • Ligands
  • Molecular Structure
  • Nitrogen / chemistry*
  • Polymers / chemistry
  • X-Ray Diffraction

Substances

  • Alkynes
  • Azides
  • Ligands
  • Polymers
  • Copper
  • Nitrogen