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 Reaction, Schiemann 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, Synthesis, 2007, 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, Synthesis, 2008, 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., 2008, 10, 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, Synthesis, 2013, 45, 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, Synlett, 2014, 25, 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., 2006, 71, 3332-3334.

Synthesis And Properties Of Bis(hetaryl)azo Dyes
M. Wang, K. Funabiki, M. Matsui, Dyes And Pigments, 2003, 57, 77-86.