Synthesis of hindered anilines: copper-catalyzed electrophilic amination of aryl boronic esters

Angew Chem Int Ed Engl. 2012 Apr 16;51(16):3953-6. doi: 10.1002/anie.201200480. Epub 2012 Mar 7.

Abstract

No longer a hindrance: copper-catalyzed electrophilic amination of aryl boronic esters is accomplished under mild reaction conditions using 2.5-5.0 mol % of a catalyst derived from copper tert-butoxide and Xantphos ligand. The reaction tolerates a wide range of functional groups and can be used to prepare some of the most hindered anilines made to date.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amination
  • Aniline Compounds / chemistry*
  • Boron / chemistry*
  • Catalysis
  • Copper / chemistry*
  • Esters
  • Phosphines / chemistry
  • Xanthenes / chemistry

Substances

  • Aniline Compounds
  • Esters
  • Phosphines
  • Xanthenes
  • Copper
  • Boron
  • xantphos
  • aniline