Catalytic Oxidative Carbonylation of Amino Moieties to Ureas, Oxamides, 2-Oxazolidinones, and Benzoxazolones

ChemSusChem. 2015 Jul 8;8(13):2204-11. doi: 10.1002/cssc.201500343. Epub 2015 Jun 18.

Abstract

The direct syntheses of ureas, oxamides, 2-oxazolidinones, and benzoxazolones by the oxidative carbonylation of amines, β-amino alcohols, and 2-aminophenols allows us to obtain high value added molecules, which have a large number of important applications in several fields, from very simple building blocks. We have found that it is possible to perform these transformations using the PdI2 /KI catalytic system in an ionic liquid, such as 1-butyl-3-methylimidazolium tetrafluoroborate, as the solvent, the solvent/catalyst system can be recycled several times with only a slight loss of activity, and the product can be recovered easily by crystallization.

Keywords: amines; amino alcohols; carbonylation; ionic liquids; palladium.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry
  • Amino Alcohols / chemistry
  • Aminophenols / chemistry
  • Benzoxazoles / chemistry*
  • Catalysis
  • Imidazoles / chemistry
  • Ionic Liquids / chemistry
  • Oxamic Acid / analogs & derivatives*
  • Oxamic Acid / chemistry
  • Oxazolidinones / chemistry*
  • Oxidation-Reduction
  • Palladium / chemistry
  • Urea / chemistry*

Substances

  • 1-butyl-3-methylimidazolium tetrafluoroborate
  • Amines
  • Amino Alcohols
  • Aminophenols
  • Benzoxazoles
  • Imidazoles
  • Ionic Liquids
  • Oxazolidinones
  • benzoxazolone
  • Palladium
  • Urea
  • Oxamic Acid
  • oxamide