C-H functionalization of 1,4-naphthoquinone by oxidative coupling with anilines in the presence of a catalytic quantity of copper(II) acetate

J Org Chem. 2011 Jul 1;76(13):5264-73. doi: 10.1021/jo200354u. Epub 2011 Jun 9.

Abstract

The oxidative addition of anilines (2) with 1,4-naphthoquinone (3) to give N-aryl-2-amino-1,4-naphthoquinones (1) was found to be catalyzed by copper(II) acetate. In the absence of the catalyst, the reactions are slower and give lower yields with the formation of many colateral products. In the presence of 10 mol % hydrated copper(II) acetate, the reactions are generally more efficient in that they are cleaner, higher yielding, and faster.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aniline Compounds / chemistry*
  • Catalysis
  • Molecular Structure
  • Naphthoquinones / chemical synthesis*
  • Naphthoquinones / chemistry*
  • Organometallic Compounds / chemistry*
  • Oxidation-Reduction
  • Stereoisomerism

Substances

  • Aniline Compounds
  • Naphthoquinones
  • Organometallic Compounds
  • cupric acetate
  • 1,4-naphthoquinone
  • aniline