Palladium-catalyzed cascade aryl addition/intramolecular lactonization of phthalaldehyde to access 3-aryl- and alkenylphthalides

J Org Chem. 2010 Sep 3;75(17):6043-5. doi: 10.1021/jo101203b.

Abstract

A palladium-catalyzed addition of arylboronic acids to phthalaldehyde, followed by an intramolecular lactonization to access 3-substituted phthalides, is described. The procedure tolerates a series of functional groups, such as methoxyl, fluoro, chloro, and trifluoromethyl groups. It represents a procedure for the synthesis of 3-substituted phthalides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzofurans / chemical synthesis*
  • Benzofurans / chemistry
  • Boronic Acids / chemistry
  • Catalysis
  • Cyclization
  • Lactones / chemistry*
  • Molecular Structure
  • Palladium / chemistry*
  • Stereoisomerism
  • o-Phthalaldehyde / chemistry*

Substances

  • Benzofurans
  • Boronic Acids
  • Lactones
  • Palladium
  • o-Phthalaldehyde
  • phthalide