Palladium-Catalyzed Multicomponent Cascade Reaction of 3-Hydroxypropionitrile: Synthesis of Substituted Dihydrochalcones

J Org Chem. 2023 Jul 7;88(13):9187-9198. doi: 10.1021/acs.joc.3c00769. Epub 2023 Jun 9.

Abstract

Direct access to substituted dihydrochalcones from the easily available starting materials 3-hydroxypropionitrile derivatives and arylboronic acids is described. The procedure involves a multicomponent aryl addition/hydroxyl elimination/reduction Heck approach in the presence of a Pd catalyst with excellent functional group tolerance and a wide range of substrates. In addition, mixed 1,3-diarylation of 3-hydroxypropanenitrile using two arylboronic acids with different electronic properties was also achieved.

MeSH terms

  • Boronic Acids* / chemistry
  • Catalysis
  • Molecular Structure
  • Palladium* / chemistry

Substances

  • Palladium
  • dihydrochalcone
  • Boronic Acids