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Diazotisation

Lianyungang Klinechem Co.,Ltd | Updated: Dec 05, 2018

Diazotisation

The nitrosation of primary aromatic amines with nitrous acid (generated in situ from sodium nitrite and a strong acid, such as hydrochloric acid, sulfuric acid, or HBF4) leads to diazonium salts, which can be isolated if the counterion is non-nucleophilic.

Diazonium salts are important intermediates for the preparation of halides (Sandmeyer ReactionSchiemann Reaction), and azo compounds. Diazonium salts can react as pseudohalide-type electrophiles, and can therefore be used in specific protocols for the Heck Reaction or Suzuki Coupling.

The intermediates resulting from the diazotization of primary, aliphatic amines are unstable; they are rapidly converted into carbocations after loss of nitrogen, and yield products derived from substitution, elimination or rearrangement processes.


Mechanism of Diazotisation

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, Synthesis2007, 81-84.


Sulfonic Acid Based Cation-Exchange Resin: A Novel Proton Source for One-Pot Diazotization-Iodination of Aromatic Amines in Water
V. D. Filimonov, N. I. Semenischeva, E. A. Krasnokutskaya, A. N. Tretyakov, H. Y. Hwang, K.-W. Chi, Synthesis2008, 185-187.


Unusually Stable, Versatile, and Pure Arenediazonium Tosylates: Their Preparation, Structures, and Synthetic Applicability
V. D. Filimonov, M. Trusova, P. Postnikov, E. A. Krasnokutskaya, Y. M. Lee, H. Y. Hwang, H. Kim, K.-W. Chi, Org. Lett.200810, 3961-3964.


A Simple and Effective Synthesis of Aryl Azides via Arenediazonium Tosylates
K. V. Kutonova, M. E. Trusova, P. S. Postnikov, V. D. Filimonov, J. Parello, Synthesis201345, 2706-2710.


Methanol-Promoted Borylation of Arylamines: A Simple and Green Synthetic Method to Arylboronic Acids and Arylboronates
C.-J. Zhao, D. Xue, Z.-H. Jia, C. Wang, J. Xiao, Synlett201425, 1577-1584.


Efficient Synthesis of 2-Amino Acid by Homologation of β2-Amino Acids Involving the Reformatsky Reaction and Mannich-Type Imminium Electrophile
R. Moumne, S. Lavielle, P. Karoyan, J. Org. Chem.200671, 3332-3334.


Synthesis and properties of bis(hetaryl)azo dyes
M. Wang, K. Funabiki, M. Matsui, Dyes and Pigments200357, 77-86.


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