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Keywords:

  • aromatic substitution;
  • arylation;
  • C[BOND]C coupling;
  • palladium;
  • synthetic methods
Thumbnail image of graphical abstract

Ipso, meta, and para: Benzoic acid derivatives can be highly regioselectively substituted at the ipso, meta, and para positions. The reaction sequence comprises an alkylative Birch reduction, a 4-alkylation, a palladium-catalyzed γ-arylation, and an oxidative rearomatization (see scheme). All the reactions are robust and experimentally easy to conduct.