Palladium-catalyzed oxidative cyclization of 3-phenoxyacrylates: an approach to construct substituted benzofurans from phenols

J Org Chem. 2011 Jun 3;76(11):4692-6. doi: 10.1021/jo200317f. Epub 2011 May 4.

Abstract

In this paper, a novel and applicable synthesis of benzofurans from commercially available phenols and propiolate through the direct oxidative cyclization has been developed. In the presence of Pd(OAc)(2)/PPh(3) and CF(3)CO(2)Ag, (E)-type 3-phenoxyacrylates underwent reaction smoothly to generate the corresponding benzofurans in good yields in benzene at 110 °C under the air pressure. In addition, this transformation of phenols into benzofurans can also be carried out in one pot. The process was simple and efficient. A tentative mechanism of palladium-catalyzed oxidative cyclization of 3-phenoxyacrylates was proposed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acrylates / chemical synthesis*
  • Acrylates / chemistry*
  • Benzofurans / chemistry*
  • Catalysis
  • Cyclization
  • Oxidation-Reduction
  • Palladium / chemistry*
  • Phenols / chemistry*

Substances

  • Acrylates
  • Benzofurans
  • Phenols
  • Palladium
  • acrylic acid
  • benzofuran