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Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

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

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

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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.
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Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

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Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
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Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

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Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
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Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

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Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
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1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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

3.9K
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...
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Silicon-Based Azo Compound-Mediated CO Activation and N2 Release.

Da Jin1, Alexander Hinz1, Xiaofei Sun1

  • 1Institute of Inorganic Chemistry, Karlsruhe Institute of Technology (KIT), Kaiserstr. 12, 76131, Karlsruhe, Germany.

Angewandte Chemie (International Ed. in English)
|September 27, 2025
PubMed
Summary

Researchers synthesized a novel silicon-based azo compound, enabling the activation of small molecules like carbon monoxide. This discovery opens new avenues for silicon in multi-electron redox chemistry, traditionally dominated by transition metals.

Keywords:
Azo compoundsCO activationMain groupSilicon–nitrogen multiple bondingSilylene

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Area of Science:

  • Organosilicon Chemistry
  • Main-group Chemistry
  • Inorganic Synthesis

Background:

  • Silicon-nitrogen compounds are crucial in main-group chemistry.
  • Silicon-substituted azo compounds with Si─N═N─Si linkages are synthetically challenging.
  • Classical iminosilane formation pathways are well-established.

Purpose of the Study:

  • To synthesize and characterize a novel silicon-based azo compound.
  • To investigate the reactivity of this silicon-azo species with small molecules.
  • To explore silicon's potential in multi-electron redox chemistry.

Main Methods:

  • Reaction of a mixed-valent silaiminyl-silylene precursor with a bulky organic azide.
  • Treatment of the synthesized silicon-azo compound with carbon monoxide (CO).
  • Reaction with iron pentacarbonyl (Fe(CO)5).

Main Results:

  • A thermally stable Si(IV)-azo species was successfully synthesized.
  • The silicon-azo compound activated CO, leading to N2 extrusion and formation of a bridged Si(II)/Si(IV) product.
  • Reaction with Fe(CO)5 resulted in N2 release and CO cleavage, with the Fe(CO)4 fragment coordinating to silicon.
  • Ligand rearrangement incorporated the carbon atom into a DippNC byproduct.

Conclusions:

  • This study reports the first synthesis of a silicon-based azo compound.
  • The compound mediates small-molecule activation, showcasing silicon's redox capabilities.
  • These findings expand the scope of silicon chemistry and its potential in catalysis.