Efficient catalyst-free bi- and triaroylation of aromatic rings in a single step

J Org Chem. 2008 Nov 21;73(22):9184-7. doi: 10.1021/jo801890e. Epub 2008 Oct 25.

Abstract

The exceptional leaving group ability of the trimethylstannyl group in electrophilic aromatic substitutions makes possible the synthesis, in a single step, of bi- and triaroylarenes through the catalyst-free, regioselective reaction of bi- and tristannylarenes with different aroyl halides in o-dichlorobenzene as solvent. Specific di- and triketones are obtained in good to excellent yields (45-83%).

MeSH terms

  • Catalysis
  • Halogens / chemistry
  • Polycyclic Aromatic Hydrocarbons / chemistry*
  • Tin Compounds / chemistry

Substances

  • Halogens
  • Polycyclic Aromatic Hydrocarbons
  • Tin Compounds
  • stannane