From N-benzoylpyridinium imides to pyrazolo[1,5-a]pyridines: a mechanistic discussion on a stoichiometric Cu protocol

Org Biomol Chem. 2013 Jun 21;11(23):3894-902. doi: 10.1039/c3ob40448j.

Abstract

A Cu-mediated preparation of 2-substitiuted pyrazolo[1,5-a]pyridines from N-benzoylpyridinium imides and terminal alkynes is described using stoichiometric Cu(OAc)2 as both the mediator and the oxidant. Extensive DFT calculations suggest a Cu(III) intermediate via disproportionation of Cu(II).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Copper / chemistry*
  • Imides / chemistry*
  • Models, Molecular
  • Molecular Conformation
  • Pyridines / chemistry*
  • Pyridinium Compounds / chemistry*
  • Quantum Theory

Substances

  • Imides
  • Pyridines
  • Pyridinium Compounds
  • Copper