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Keywords:

  • arenes;
  • catalysis;
  • C[BOND]H functionalization;
  • halogenation;
  • palladium
Thumbnail image of graphical abstract

Reducing the load: A facile palladium-catalyzed ortho-selective bromination and chlorination of anilides occurs under aerobic conditions at room temperature when N-halosuccinimides (NXS) are used in the presence of p-toluenesulfonic acid (PTSA). The orthopalladated PTSA complex is not only catalytically competent but also undergoes a reductive process to yield an unusual PdI–PdII tetramer (see structure; Pd green, O red, S yellow, C gray).