Tetrazole synthesis via the palladium-catalyzed three component coupling reaction

Shin Kamijo, Tetsuo Kin, Zhibao Huo, Young Soo Gyoung, Jae Goo Shim, Yoshinori Yamamoto

Research output: Contribution to journalArticlepeer-review

18 Citations (Scopus)

Abstract

The synthesis of tetrazoles was achieved via the palladium-catalyzed three component coupling (TCC) reaction; The TCC reaction of malononitrile derivatives, allyl acetate and trimethylsilyl azide proceeds very smoothly under a catalytic amount of Pd(PPh3)4 to give 2-allyltetrazoles, and further the TCC reaction of various activated cyano compounds, allyl methyl carbonate and trimethylsilyl azide proceeds readily under a catalytic amount of Pd2(dba)3 · CHCl 3 and (2-furyl)3P to give 2-allyltetrazoles. π-Allylpalladium azide complex is proposed as a key intermediate in the catalytic cycle and the [3 + 2] cycloaddition between the π-allylpalladium azide complex and cyano compounds most probably gives the tetrazole frameworks. The deallylation of the derived allyltetrazoles was attained via the two-step procedure; the ruthenium-catalyzed isomerization and ozonolysis.

Original languageEnglish
Pages (from-to)181-192
Number of pages12
JournalMolecular Diversity
Volume6
Issue number3-4
DOIs
Publication statusPublished - 2003 Dec 1

Keywords

  • Allyl acetate
  • Allyl carbonate
  • Cyano compound
  • Palladium catalyst
  • Tetrazole
  • Three component coupling reaction
  • Trimethylsilyl azide

ASJC Scopus subject areas

  • Catalysis
  • Information Systems
  • Molecular Biology
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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