A palladium-catalyzed alkylation/direct arylation synthesis of nitrogen-containing heterocycles

J Org Chem. 2008 Mar 7;73(5):1888-97. doi: 10.1021/jo702052b. Epub 2008 Feb 9.

Abstract

A norbornene-mediated palladium-catalyzed sequence is described in which an alkyl-aryl bond and an aryl-heteroaryl bond are formed in one reaction vessel. The aryl-heteroaryl bond-forming step occurs via a direct arylation reaction. A number of six-, seven-, and eight-membered ring-annulated indoles, pyrroles, pyrazoles, and azaindoles were synthesized from the corresponding bromoalkyl azole and an aryl iodide.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Catalysis
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Nitrogen / chemistry*
  • Palladium / chemistry*

Substances

  • Heterocyclic Compounds
  • Palladium
  • Nitrogen