Copper-catalyzed oxidative C-O bond formation of 2-acyl phenols and 1,3-dicarbonyl compounds with ethers: direct access to phenol esters and enol esters

J Org Chem. 2014 May 16;79(10):4735-42. doi: 10.1021/jo500576x. Epub 2014 Apr 30.

Abstract

A copper-catalyzed oxidative coupling of 2-carbonyl-substituted phenols and 1,3-dicarbonyl compounds with a wide range of dibenzyl or dialkyl ethers is described. This protocol provides an efficient preparation of phenol esters and enol esters in good yields with high chemoselectivity. This method represents an alternative protocol for classical esterification reactions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzyl Compounds / chemistry*
  • Catalysis
  • Copper / chemistry*
  • Esterification
  • Esters
  • Ethers / chemical synthesis*
  • Ethers / chemistry*
  • Molecular Structure
  • Oxidation-Reduction
  • Phenols / chemical synthesis*
  • Phenols / chemistry*

Substances

  • Benzyl Compounds
  • Esters
  • Ethers
  • Phenols
  • Copper