Gattermann reaction

What is Gattermann reaction?

In 1890, Gattermann reported the reaction for synthesizing aromatic halides or cyanides by decomposing corresponding diazo salts with copper powder, freshly obtained from copper (II) sulfate aqueous solution.

Gattermann reaction - general reaction scheme - Gattermann method
Gattermann reaction

X = Cl, Br, I, CN, etc.

This reaction is commonly known as the Gattermann reaction or Gattermann method, and it shares similarities with the Sandmeyer reaction. A radical mechanism involving electron transfer at the surface of metallic copper is believed to be the underlying mechanism. It is important to note that this reaction cannot be used to prepare aromatic fluorides due to the presence of HF, which ionizes into H and HF2 ions.

The synthesis of aromatic halides and cyanides can be achieved through Gattermann reaction.

References

Gattermann, L. (1890), Untersuchungen über Diazoverbindungen. [Studies on diazo compounds] Ber. Dtsch. Chem. Ges., 23: 1218-1228. https://doi.org/10.1002/cber.189002301199

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