Direct Transformation of Arylamines to Aryl Halides via Sodium Nitrite and N-Halosuccinimide

A one-pot universal approach for transforming arylamines to aryl halides via reaction with sodium nitrite (NaNO2 ) and N-halosuccinimide (NXS) in DMF at room temperature under metal- and acid-free condition is described. This new protocol that is complementary to the Sandmeyer reaction, is suggested to involve the in situ generation of nitryl halide induce nitrosylation of aryl amine to form the diazo intermediate which is halogenated to furnish the aryl halide.