Synthesis of 5-substituted 1H-tetrazoles by the copper-catalyzed [3+2] cycloaddition of nitriles and trimethylsilyl azide

Tienan Jin, Fukuzou Kitahara, Shin Kamijo, Yoshinori Yamamoto

Research output: Contribution to journalArticle

42 Citations (Scopus)

Abstract

The copper-catalyzed [3+2] cycloaddition between various nitriles and trimethylsilyl azide in DMF/MeOH produced the corresponding 5-substituted 1H-tetrazoles in good to high yields. It was proposed that the reaction proceeds through the formation in situ of a copper azide species and subsequent [3+2] cycloaddition with the nitriles. Furthermore, we found that a copper and triethylamine combined catalyst also promoted the cycloaddition of nitriles and trimethylsilyl azide to afford the 5-substituted 1H-tetrazoles at relatively low reaction temperatures. The copper azide species would be formed by reaction of the copper catalyst with Et3N·HN3 generated in situ.

Original languageEnglish
Pages (from-to)1575-1580
Number of pages6
JournalChemistry - An Asian Journal
Volume3
Issue number8-9
DOIs
Publication statusPublished - 2008 Sep 1

Keywords

  • Copper
  • Cycloaddition
  • Homogeneous catalysis
  • Nitriles
  • Tetrazoles

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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