Copper-catalyzed synthesis of N-unsubstituted 1,2,3-triazoles from nonactivated terminal alkynes

Tetsuo Kin, Shin Kamijo, Yoshinori Yamamoto

Research output: Contribution to journalArticlepeer-review

149 Citations (Scopus)

Abstract

The [3+2] cycloaddition of nonactivated terminal alkynes and trimethylsilyl azide proceeded smoothly in the presence of CuI catalyst and DMF/MeOH, to give the corresponding N-unsubstituted triazoles in good to high yields. The reaction most probably proceeds through the in situ formation of a copper acetylide species and hydrazoic acid, followed by a successive [3+2] cycloaddition reaction.

Original languageEnglish
Pages (from-to)3789-3791
Number of pages3
JournalEuropean Journal of Organic Chemistry
Issue number18
DOIs
Publication statusPublished - 2004 Sep 13

Keywords

  • 1,2,3-Triazoles
  • Alkynes
  • Catalysis
  • Copper
  • Cycloaddition

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Copper-catalyzed synthesis of N-unsubstituted 1,2,3-triazoles from nonactivated terminal alkynes'. Together they form a unique fingerprint.

Cite this