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Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

6.4K
The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
6.4K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.2K
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,...
2.2K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

4.1K
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
4.1K
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

4.0K
Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
4.0K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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

4.0K
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.
4.0K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

2.9K
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.
2.9K

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Related Experiment Video

Updated: Sep 6, 2025

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

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Vinylogous Nitro-Haloform Reaction Enables Aromatic Amination.

Claudio Monasterolo1, Mauro F A Adamo1

  • 1Centre for Synthesis and Chemical Biology, Department of Chemistry, Royal College of Surgeons in Ireland, Dublin 2, Ireland.

Organic Letters
|June 28, 2022
PubMed
Summary

This study introduces a novel aromatic haloform reaction for metal-free arene functionalization. It enables efficient aromatic amination of heteroarenes, yielding N-functionalized products without transition metals.

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Area of Science:

  • Organic Chemistry
  • Synthetic Methodology
  • Catalysis

Background:

  • Traditional aromatic functionalization often relies on transition-metal catalysis, posing challenges in cost and purification.
  • Developing metal-free synthetic routes is crucial for sustainable and economical chemical synthesis.
  • The haloform reaction is a well-established transformation, but its application to aromatic systems is limited.

Purpose of the Study:

  • To report the first example of an aromatic haloform reaction for arene functionalization.
  • To establish a metal-free approach for the amination of heteroarenes.
  • To develop new N-protection strategies using this novel methodology.

Main Methods:

  • Utilized heteroarenes with a vinylogous nitromethane system.
  • Employed a trichloromethane derivative intermediate.
  • Performed haloform-type amination under metal-free conditions.

Main Results:

  • Achieved quantitative yields of N-functionalized arenes from heteroarenes.
  • Demonstrated a novel, metal-free aromatic amination pathway.
  • Successfully applied the method to create effective orthogonal N-protection strategies.

Conclusions:

  • A new haloform-type approach provides a metal-free functionalization of arenes.
  • This method offers a promising route for synthesizing N-functionalized arenes.
  • A new N-protecting reagent was established, highlighting the versatility of the reaction.