Efficient synthesis of sterically crowded biaryls by palladium-phosphinous acid-catalyzed cross-coupling of aryl halides and aryl grignards

J Org Chem. 2008 Jan 4;73(1):162-7. doi: 10.1021/jo701893m. Epub 2007 Dec 6.

Abstract

A series of sterically hindered biaryls have been obtained by palladium- and nickel-phosphinous acid-catalyzed Kumada-Corriu cross-coupling of ortho-substituted aryl halides and Grignard reagents. This method allows formation of di- and tri-ortho-substituted biaryls in 87-98% yield under mild reaction conditions even when electron-rich aryl chlorides are used. The reaction also proceeds with aryl iodides at -20 degrees C, and under these conditions, functional groups that are generally not compatible with Grignard reagents are tolerated.

MeSH terms

  • Biphenyl Compounds / chemical synthesis*
  • Biphenyl Compounds / chemistry
  • Catalysis
  • Hydrocarbons, Halogenated / chemistry*
  • Ligands
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Palladium / chemistry*
  • Phosphorus Acids / chemistry*
  • Stereoisomerism

Substances

  • Biphenyl Compounds
  • Hydrocarbons, Halogenated
  • Ligands
  • Organometallic Compounds
  • Phosphorus Acids
  • Palladium