Direct Synthesis of 3-Aryl Substituted Isocoumarins and Phthalides through Palladium Acetate Catalyzed C(sp2 )-H Activation in Ionic Liquids

Chemistry. 2022 Nov 21;28(65):e202202350. doi: 10.1002/chem.202202350. Epub 2022 Sep 19.

Abstract

A novel Pd-catalysed oxidative coupling between benzoic acids and vinylarenes or acrylates to furnish isocoumarins and phthalides is reported. The reaction proceeds smoothly in molten tetrabutylammonium acetate via a selective C-H bond activation, with very low percentage of ligand-free palladium acetate as the catalyst, under atmospheric pressure of oxygen. Sub-stoichiometric amount of copper acetate is also required as a reoxidant for the palladium.

Keywords: C−H activation; benzylidenephthalide; ionic liquid; isocoumarin; palladium catalysis.

MeSH terms

  • Acetates
  • Catalysis
  • Ionic Liquids*
  • Isocoumarins / chemistry
  • Palladium* / chemistry

Substances

  • Palladium
  • Isocoumarins
  • phthalide
  • Ionic Liquids
  • Acetates