Synthesis of triazoles from nonactivated terminal alkynes via the three-component coupling reaction using a Pd(0)-Cu(I) bimetallic catalyst

Shin Kamijo, Tetsuo Kin, Zhibao Huo, Yoshinori Yamamoto

Research output: Contribution to journalArticlepeer-review

177 Citations (Scopus)

Abstract

The synthesis of triazoles via the three-component coupling reaction of unactivated terminal alkynes, allyl carbonate, and trimethylsiyl azide under the Pd(0)-Cu(I) bimetallic catalyst is developed. The reaction most probably proceeds through the formation of a π-allylpalladium azide complex and a copper-acetylide followed by a successive [3 + 2] cycloaddition. The deallylation of the resulting allyltriazoles proceeds very easily by the Ru-catalyzed isomerization followed by the ozonolysis of the resulting propenyltriazoles to give the triazoles in high yields.

Original languageEnglish
Pages (from-to)7786-7787
Number of pages2
JournalJournal of the American Chemical Society
Volume125
Issue number26
DOIs
Publication statusPublished - 2003 Jul 2

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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