Zinc mediated azide-alkyne ligation to 1,5- and 1,4,5-substituted 1,2,3-triazoles

Org Lett. 2013 Sep 20;15(18):4826-9. doi: 10.1021/ol402225d. Epub 2013 Sep 3.

Abstract

A mild method for regioselective formation of 1,5-substituted 1,2,3-triazoles is described. The zinc-mediated reaction works at room temperature and is successful across a wide range of azido/alkynyl substrates. Additionally, the triazole 4-position can be further functionalized through the intermediate aryl-zinc to accommodate a diverse three-component coupling strategy.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Azides / chemistry*
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Cyclization
  • Ligation
  • Molecular Structure
  • Triazoles / chemical synthesis*
  • Triazoles / chemistry
  • Zinc / chemistry*

Substances

  • Alkynes
  • Azides
  • Triazoles
  • Zinc