Pd(II)-Catalyzed Aminotetrazole-Directed Ortho-Selective Halogenation of Arenes

A Pd­(II)-catalyzed ortho-selective halogenation of N-aryl ring of N,1-diaryl-1H-tetrazol-5-amine has been described employing N-halosuccinimide as a halogen source via C–H bond activation. The present work features 5-aminotetrazole, as a directing group, for the chemo- and regioselective C–H halogenation of arenes. The kinetic isotope study (kH/kD = 2.9) suggests that the cleavage of the C–H bond takes place in the rate-determining step. The scope and mechanism of the protocol have been demonstrated.