Pd(II)-catalyzed aminotetrazole-directed ortho-selective halogenation of arenes.J Org Chem. 2013 Jun 21; 78(12):6104-11.JO
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.