Room-Temperature Cu(II)-Catalyzed Chemo- and Regioselective Ortho-Nitration of Arenes via C–H Functionalization

An efficient Cu-catalyzed chemo- and regioselective ortho-nitration of N,1-diaryl-5-aminotetrazoles and N,4-diaryl-3-amino-1,2,4-triazoles has been described with good functional group compatibility. The procedure features the use of an operationally simple protocol utilizing the commercially available less toxic CuCl₂·2H₂O as catalyst and Fe­(NO₃)₃·9H₂O as nitration source at room temperature. Removal of the 5-aminotetrazole directing group has been demonstrated using base hydrolysis to afford substituted 2-nitroanilines.