Highly regioselective N-2 arylation of 4,5-dibromo-1,2,3-triazole: efficient synthesis of 2-aryltriazoles

Org Lett. 2009 Nov 5;11(21):5026-8. doi: 10.1021/ol9019875.

Abstract

Reaction of 4,5-dibromo-1,2,3-triazole with electron-deficient aromatic halides in the presence of potassium carbonate in DMF produces the corresponding 2-aryl-4,5-dibromotriazoles with high regioselectivity. Subsequent debromination of these triazoles by hydrogenation furnishes 2-aryltriazoles in excellent yields. Overall, this two-step process provides an efficient access to 2-aryl-1,2,3-triazoles.

MeSH terms

  • Catalysis
  • Combinatorial Chemistry Techniques
  • Hydrocarbons, Brominated
  • Hydrogenation
  • Molecular Structure
  • Stereoisomerism
  • Triazoles / chemical synthesis*
  • Triazoles / chemistry

Substances

  • 4,5-dibromo-1,2,3-triazole
  • Hydrocarbons, Brominated
  • Triazoles