Chemoselective benzylation of unprotected anthranilic acids with benzhydryl alcohols by water-soluble Au(III)/TPPMS in water

J Org Chem. 2013 Jul 5;78(13):6714-20. doi: 10.1021/jo401064f. Epub 2013 Jun 18.

Abstract

A novel and efficient method for the benzylation of unprotected anthranilic acids with benzhydryl alcohols using water-soluble Au(III)/TPPMS in water is developed. Water plays an important role in our catalytic system. This new protocol could be used for not only N-benzylation, but also chemoselective C-benzylation by the Friedel-Crafts reaction.

MeSH terms

  • Alcohols / chemistry*
  • Benzenesulfonates / chemistry*
  • Benzhydryl Compounds / chemistry*
  • Catalysis
  • Gold / chemistry*
  • Molecular Structure
  • Phosphines / chemistry*
  • Solubility
  • Water / chemistry
  • ortho-Aminobenzoates / chemistry*

Substances

  • Alcohols
  • Benzenesulfonates
  • Benzhydryl Compounds
  • Phosphines
  • ortho-Aminobenzoates
  • Water
  • Gold