Palladium-catalyzed selective synthesis of 2-allyltetrazoles

J Org Chem. 2002 Oct 18;67(21):7413-7. doi: 10.1021/jo026147l.

Abstract

The palladium-catalyzed three-component coupling (TCC) reaction of cyano compounds, allyl methyl carbonate, and trimethylsilyl azide under a catalytic amount of Pd2(dba)3.CHCl3 (2.5 mol %) and tri(2-furyl)phosphine (10 mol %) gave various kinds of 2-allyltetrazoles in good to excellent yields. A pi-allylpalladium azide complex is proposed as a key intermediate in the TCC reaction.

MeSH terms

  • Allyl Compounds / chemical synthesis*
  • Catalysis
  • Indicators and Reagents
  • Models, Molecular
  • Molecular Conformation
  • Palladium*
  • Structure-Activity Relationship
  • Tetrazoles / chemical synthesis*

Substances

  • Allyl Compounds
  • Indicators and Reagents
  • Tetrazoles
  • Palladium