Synthesis of isocoumarins via Pd/C-mediated reactions of o-iodobenzoic acid with terminal alkynes

J Org Chem. 2005 Jun 10;70(12):4778-83. doi: 10.1021/jo050440e.

Abstract

The coupling reaction of o-iodobenzoic acid with terminal alkynes by using a catalyst system of 10% Pd/C-Et3N-CuI-PPh3 has been studied in a variety of solvents. 3-Substituted isocoumarins were formed in good yields and with good regioselectivity when the reaction was performed in EtOH.

MeSH terms

  • Alkynes / chemistry*
  • Catalysis
  • Combinatorial Chemistry Techniques*
  • Coumarins / analysis
  • Coumarins / chemical synthesis*
  • Ethanol / chemistry
  • Iodobenzoates / chemistry*
  • Molecular Structure
  • Palladium / chemistry*
  • Solvents

Substances

  • Alkynes
  • Coumarins
  • Iodobenzoates
  • Solvents
  • Ethanol
  • Palladium
  • 2-iodobenzoic acid