Cu/Pd-Catalyzed, Three-Component Click Reaction of Azide, Alkyne, and Aryl Halide: One-Pot Strategy toward Trisubstituted Triazoles

Org Lett. 2015 Jun 5;17(11):2860-3. doi: 10.1021/acs.orglett.5b01342. Epub 2015 May 22.

Abstract

A Cu/Pd-catalyzed, three-component click reaction of azide, alkyne, and aryl halide has been developed. By using this Cu/Pd transmetalation relay catalysis, a variety of 1,4,5-trisubstituted 1,2,3-triazoles were quickly assembled in one step in high yields with complete regioselectivity, just like assembling Lego bricks. Notably, different from the well-established CuAAC click reactions only working on terminal alkynes, this reaction offers an alternative solution for the problem of the click reaction of internal alkynes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Azides / chemistry*
  • Catalysis
  • Click Chemistry
  • Copper
  • Hydrocarbons, Halogenated / chemistry*
  • Molecular Structure
  • Palladium
  • Triazoles / chemical synthesis*
  • Triazoles / chemistry

Substances

  • Alkynes
  • Azides
  • Hydrocarbons, Halogenated
  • Triazoles
  • Palladium
  • Copper