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Keywords:

  • diazo compounds;
  • Heck reaction;
  • homogeneous catalysis;
  • palladium;
  • phenols

Abstract

Significantly better yields were achieved in Mizoroki–Heck reactions using 4-phenoldiazonium salts instead of their O-alkylated analogues under otherwise identical conditions. We found that a one-flask deacetylation–diazotation–precipitation sequence starting from paracetamol or acetanilides derived thereof provides a convenient access to the required diazonium tetrafluoroborates. The utility of these arylating agents in palladium-catalyzed C[BOND]C bond forming reactions was demonstrated for a one-flask-synthesis of the heterocyclic core of the drug aripiprazole. Notably, the diazonium salt formation from an acetanilide could be combined with two Pd-catalyzed steps in a one-flask sequence, without any exchange of solvents or isolation of intermediates.