Carbonylation of aryl chlorides with oxygen nucleophiles at atmospheric pressure. Preparation of phenyl esters as acyl transfer agents and the direct preparation of alkyl esters and carboxylic acids

J Org Chem. 2008 Sep 19;73(18):7096-101. doi: 10.1021/jo800907e. Epub 2008 Aug 23.

Abstract

A mild, functional group tolerant method of the preparation of phenyl esters from aryl chlorides via palladium-catalyzed carbonylation is described using atmospheric pressure of carbon monoxide. Phenyl esters are shown to be useful acylating agents, delivering libraries of carbonyl derivatives, including alkyl, allyl and thioesters, under very mild conditions. Direct preparation of alkyl esters and carboxylic acids is also demonstrated, providing the first method for the preparation of methyl and ethyl esters from aryl chlorides without pressured reactors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Atmospheric Pressure
  • Benzoates / chemical synthesis*
  • Benzoates / chemistry
  • Carbon Monoxide / chemistry*
  • Catalysis
  • Esters / chemical synthesis*
  • Esters / chemistry
  • Hydrocarbons, Chlorinated / chemistry*
  • Molecular Structure
  • Oxygen / chemistry*
  • Palladium / chemistry
  • Stereoisomerism

Substances

  • Benzoates
  • Esters
  • Hydrocarbons, Chlorinated
  • Palladium
  • Carbon Monoxide
  • Oxygen