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Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para...

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO₂ Overview

Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by...

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO₂ Mechanism

Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.

Diazonium Group Substitution: –OH and –H

Diazonium Group Substitution: –OH and –H

Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.

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Related Experiment Video

Updated: Jan 6, 2026

Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds

Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds

Published on: October 15, 2019

Modular click chemistry libraries for functional screens using a diazotizing reagent.

Genyi Meng¹, Taijie Guo¹, Tiancheng Ma¹

¹Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of the Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai, China.

|October 4, 2019

Summary

This study introduces a safe and practical method for synthesizing azides from abundant primary amines. This breakthrough expands the scope of click chemistry, particularly for copper(I)-catalysed azide-alkyne cycloaddition reactions.

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Area of Science:

Organic Chemistry
Chemical Biology
Materials Science

Background:

Click chemistry enables rapid modular synthesis of molecules with desired properties.
Copper(I)-catalysed azide-alkyne cycloaddition (CuAAC) and sulfur(VI) fluoride exchange (SuFEx) are key click reactions.
CuAAC reactions are limited by the toxicity and explosive potential of azide reagents.

Purpose of the Study:

To develop a safe and practical method for azide synthesis from primary amines.
To expand the accessibility of azide reagents for click chemistry applications.
To enhance the utility of CuAAC reactions in various scientific fields.

Main Methods:

A novel reaction for converting primary amines into azides using fluorosulfuryl azide (FSO2N3).
High-throughput synthesis of over 1,200 azides using 96-well plates.
Demonstration of the reaction's safety and practicality.

Main Results:

Successfully synthesized a large library of azides from primary amines.
Established a reliable and safe azide preparation method.
The new method is compatible with the widely used CuAAC reaction.

Conclusions:

The developed method significantly broadens the range of accessible azides and 1,2,3-triazoles.
This advancement provides a powerful tool for organic synthesis, medicinal chemistry, and materials science.
The reaction's safety and efficiency make it highly applicable in various research areas.