Copper-catalyzed direct aryl quaternization of N-substituted imidazoles to form imidazolium salts

J Org Chem. 2013 Jun 7;78(11):5723-30. doi: 10.1021/jo400527r. Epub 2013 May 10.

Abstract

Diaryliodonium salts are employed to directly quaternize N-substituted imidazoles by using a copper catalyst to construct aryl imidazolium salts in moderate to excellent yields. This transformation is tolerant to a broad range of functional groups and provides a straightforward, efficient, and versatile route to synthesize aryl imidazolium as well as triazolium salts, especially the unsymmetric version.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Copper / chemistry*
  • Imidazoles / chemical synthesis*
  • Imidazoles / chemistry*
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Salts / chemical synthesis
  • Salts / chemistry

Substances

  • Imidazoles
  • Organometallic Compounds
  • Salts
  • Copper