Further Information
Literature
Related Reactions
Azo Coupling
Diazotisation
Rosenmund-von Braun Reaction
Schiemann Reaction
Sandmeyer Reaction
The substitution of an aromatic amino group is possible via preparation of its diazonium salt and subsequent displacement with a nucleophile (Cl-, I-, CN-, RS-, HO-). Many Sandmeyer Reactions proceed under copper(I) catalysis, while the Sandmeyer-type reactions with thiols, water and potassium iodide don't require catalysis.
The Sandmeyer Reaction is a very important transformation in aromatic chemistry, because it can result in some substitution patterns that are not achievable by direct substitution.
Fluorination is possible by using the related Schiemann Reaction.
Mechanism
Recent Literature
A convenient and general one-step preparation of aromatic and some heterocyclic
iodides in good yields includes a sequential diazotization-iodination of
aromatic amines with KI, NaNO2, and p-TsOH in acetonitrile at
room temperature.
E. A. Krasnokutskaya, N. I. Semenischeva, V. D. Filimonov, P. Knochel, Synthesis, 2007, 81-84.
