DBU catalysis of N,N'-carbonyldiimidazole-mediated amidations

Org Lett. 2010 Jan 15;12(2):324-7. doi: 10.1021/ol9026599.

Abstract

1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) has been found to catalyze the amidation of acyl imidazoles. The rate acceleration is especially evident with traditionally unreactive, electron-deficient anilines. DBU is readily available and offers safety and cost advantages over more commonly employed catalysts such as 1-hydroxybenzotriazole.

MeSH terms

  • Amides / chemical synthesis*
  • Amides / chemistry
  • Bridged Bicyclo Compounds, Heterocyclic / chemistry*
  • Catalysis
  • Imidazoles / chemistry*
  • Molecular Structure

Substances

  • Amides
  • Bridged Bicyclo Compounds, Heterocyclic
  • Imidazoles
  • N,N-carbonyldiimidazole
  • 1,8-diazabicyclo(5.4.0)undec-7-ene