Mild CH Halogenation of Anilides and the Isolation of an Unusual Palladium(I)–Palladium(II) Species

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).