Room temperature palladium-catalyzed 2-arylation of indoles

J Am Chem Soc. 2006 Apr 19;128(15):4972-3. doi: 10.1021/ja060809x.


This communication describes the rational development of a PdII-catalyzed method for the direct 2-arylation of indoles using [Ar-IIII-Ar]BF4. These reactions proceed under remarkably mild conditions (often at room temperature and in the presence of ambient air and moisture), and these features are believed to be the result of a PdII/IV mechanism operating in these systems. These transformations can be used to prepare functionally diverse 2-arylated indoles and pyrroles, and their potential utility has been expanded by the development of an in situ procedure for generating the iodine(III) arylating reagents.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzene Derivatives / chemical synthesis*
  • Benzene Derivatives / chemistry
  • Catalysis
  • Indoles / chemical synthesis*
  • Indoles / chemistry*
  • Oxidation-Reduction
  • Palladium / chemistry
  • Temperature


  • Benzene Derivatives
  • Indoles
  • Palladium
  • 1-methylindole