Electrochemically initiated oxidative amination of benzoxazoles using tetraalkylammonium halides as redox catalysts

J Org Chem. 2014 Oct 17;79(20):9613-8. doi: 10.1021/jo501736w. Epub 2014 Oct 6.

Abstract

An electrochemically promoted coupling of benzoxazoles and amines has been developed, leading directly to the formation of 2-aminobenzoxazoles. The chemistry utilizes catalytic quantities of a tetraalkylammonium halide redox catalyst and is carried out under constant current conditions in a simple undivided cell. The use of excess chemical oxidant or large amounts of supporting electrolyte is avoided. This greatly simplifies the workup and isolation process and leads to a reduction in waste.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Amination
  • Benzoxazoles / chemistry*
  • Catalysis
  • Halogens / chemistry*
  • Molecular Structure
  • Oxidation-Reduction
  • Quaternary Ammonium Compounds / chemistry*

Substances

  • Benzoxazoles
  • Halogens
  • Quaternary Ammonium Compounds