Organic Chemistry Portal
Reactions >> Name Reactions

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.