Unexpected C-Se cross-coupling reaction: copper oxide catalyzed synthesis of symmetrical diaryl selenides via cascade reaction of selenourea with aryl halides/boronic acids

J Org Chem. 2010 Dec 17;75(24):8720-3. doi: 10.1021/jo102017g. Epub 2010 Nov 23.

Abstract

Selenourea is used as an effective selenium surrogate in the C-Se cross-coupling reaction catalyzed by copper oxide nanoparticles under ligand free conditions. This protocol has been utilized for the synthesis of a variety of symmetrical diaryl selenides in good to excellent yields from the readily available aryl halides/boronic acids.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Boronic Acids / chemistry*
  • Catalysis
  • Hydrocarbons, Halogenated / chemistry*
  • Ligands
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Organoselenium Compounds / chemical synthesis*
  • Organoselenium Compounds / chemistry
  • Selenium Compounds / chemical synthesis*
  • Selenium Compounds / chemistry
  • Urea / analogs & derivatives*
  • Urea / chemical synthesis
  • Urea / chemistry

Substances

  • Boronic Acids
  • Hydrocarbons, Halogenated
  • Ligands
  • Organoselenium Compounds
  • Selenium Compounds
  • selenourea
  • Urea