Pyridine-phosphinimine ligand-accelerated Cu(I)-catalyzed azide-alkyne cycloaddition for preparation of 1-(pyridin-2-yl)-1,2,3-triazole derivatives

Org Biomol Chem. 2014 Aug 21;12(31):5954-63. doi: 10.1039/c4ob01176g.

Abstract

A series of phosphinimine ligands were designed and used in the Cu(i)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction of tetrazolo[1,5-a]pyridines and alkynes for the first time. By optimizing the reaction conditions, an efficient catalytic system (CuCl/2-PyCH2N[double bond, length as m-dash]P(t)Bu3) was developed to give 1-(pyridin-2-yl)-1,2,3-triazole derivatives in moderate to excellent yields (46-98%).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Azides / chemistry*
  • Catalysis
  • Copper / chemistry*
  • Cycloaddition Reaction*
  • Imines / chemistry*
  • Ligands
  • Molecular Conformation
  • Pyridines / chemistry*
  • Triazoles / chemical synthesis*
  • Triazoles / chemistry

Substances

  • Alkynes
  • Azides
  • Imines
  • Ligands
  • Pyridines
  • Triazoles
  • Copper
  • pyridine