Decarboxylative etherification of aromatic carboxylic acids

J Am Chem Soc. 2012 Jun 20;134(24):9938-41. doi: 10.1021/ja304539j. Epub 2012 Jun 8.

Abstract

Decarboxylative Chan-Evans-Lam-type couplings are presented as a new strategy for the regiospecific construction of diaryl and alkyl aryl ethers starting from easily available aromatic carboxylic acids. They allow converting various aromatic carboxylate salts into the corresponding aryl ethers by reaction with alkyl orthosilicates or aryl borates, under aerobic conditions in the presence of silver carbonate as the decarboxylation catalyst and copper acetate as the cross-coupling catalyst.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbonates / chemistry
  • Carboxylic Acids / chemistry*
  • Catalysis
  • Copper / chemistry
  • Decarboxylation
  • Ethers / chemistry*
  • Hydrocarbons, Aromatic / chemistry*
  • Silver Compounds / chemistry
  • Stereoisomerism

Substances

  • Carbonates
  • Carboxylic Acids
  • Ethers
  • Hydrocarbons, Aromatic
  • Silver Compounds
  • Copper
  • silver carbonate