Four-component coupling reactions of silylacetylenes, allyl carbonates, and trimethylsilyl azide catalyzed by a Pd(0)-Cu(I) bimetallic catalyst. Fully substituted triazole synthesis from seemingly internal alkynes

Shin Kamijo, Tetsuo Kin, Yoshinori Yamamoto

Research output: Contribution to journalArticle

58 Citations (Scopus)

Abstract

Fully substituted triazoles were synthesized via the four-component coupling reaction of unactivated silylacetylenes, two equivalents of allyl carbonates, and trimethylsilyl azide in the presence of a Pd(0)-Cu(I) bimetallic catalyst. Various trisubstituted 1,2,3-triazoles were obtained in good yields. The reaction most probably proceeds through the [3+2] cycloaddition reaction between the alkynylcopper species and azide followed by the cross-coupling reaction between the vinylcopper intermediate and π-allylpalladium complex.

Original languageEnglish
Pages (from-to)689-691
Number of pages3
JournalTetrahedron Letters
Volume45
Issue number4
DOIs
Publication statusPublished - 2004 Jan 19

Keywords

  • Bimetallic catalyst
  • Copper catalyst
  • Four-component coupling
  • Palladium catalyst
  • TMS-azide
  • Triazole
  • π-Allylpalladium complex

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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