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Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

2.8K
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.
2.8K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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

3.8K
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.
3.8K
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

3.0K
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...
3.0K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.1K
Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
2.1K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

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

1.9K
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...
1.9K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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

3.3K
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...
3.3K

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Recent advances in electrochemical functionalization using diazonium salts.

Krishna Kher1, Mukesh Dhaker1, Prabhat Kumar Baroliya1

  • 1Department of Chemistry, Mohanlal Sukhadia University, Udaipur, India. prabhatkbaroliya@mlsu.ac.in.

Organic & Biomolecular Chemistry
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Summary

Organic electrochemical synthesis using arenediazonium salts offers a sustainable alternative to traditional methods. This approach avoids hazardous reductants, enabling milder conditions and faster reactions for diverse functionalizations.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Electrochemistry

Background:

  • Arenediazonium salts are versatile synthetic precursors.
  • Traditional dediazoniation methods often employ toxic oxidants and expensive catalysts, limiting cost-effectiveness and sustainability.
  • Recent advancements in organic electrochemistry offer promising alternatives.

Purpose of the Study:

  • To review recent advances in facile organic electrochemical syntheses utilizing arenediazonium salt precursors.
  • To highlight methods that avoid the use of hazardous reductants.
  • To showcase the benefits of electrochemical approaches in terms of reaction conditions and time.

Main Methods:

  • Electrochemical reduction of arenediazonium salts *in situ*.
  • Application of mild reaction conditions.
  • Facilitation of diverse functionalizations.

Main Results:

  • Demonstration of facile organic electrochemical syntheses using arenediazonium salts.
  • Avoidance of hazardous reductants in the synthetic procedures.
  • Achieved functionalizations under mild conditions with shorter reaction times.

Conclusions:

  • Organic electrochemistry provides a sustainable and efficient platform for arenediazonium salt transformations.
  • Electrochemical methods overcome the limitations of traditional synthetic routes.
  • This approach facilitates greener and more economical chemical synthesis.