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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
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

8.9K
Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
8.9K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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

4.1K
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.
4.1K
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
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

3.2K
The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...
3.2K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

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

2.0K
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...
2.0K

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Triazolium Salts as Lewis Acid Catalysts.

Deepak Ranolia1, Idan Avigdori1, Kuldeep Singh1

  • 1Schulich Faculty of Chemistry, Technion - Israel Institute of Technology, Technion City, Haifa 32000, Israel.

Organic Letters
|May 26, 2022
PubMed
Summary

Researchers developed novel tetraaryl-1,2,3-triazolium salts as potent Lewis acid catalysts. These compounds efficiently catalyze hydrosilylation-deoxygenation reactions under mild conditions, offering a new tool for organic synthesis.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Materials Science

Background:

  • Nitrenium ions are reactive intermediates with potential as Lewis acids.
  • Developing stable and effective Lewis acid catalysts is crucial for organic synthesis.
  • Previous nitrenium salts have shown limited catalytic activity.

Purpose of the Study:

  • To synthesize and characterize a new class of nitrenium-based Lewis acids: tetraaryl-1,2,3-triazolium salts.
  • To evaluate the catalytic activity of these novel salts in organic transformations.
  • To establish triazolium ions as a viable platform for Lewis acid catalysis.

Main Methods:

  • Synthesis of tetraaryl-1,2,3-triazolium salts.
  • Characterization using Nuclear Magnetic Resonance (NMR) spectroscopy and X-ray crystallography.
  • Determination of Gutmann-Beckett acidity numbers.
  • Catalytic testing in hydrosilylation-deoxygenation reactions.

Main Results:

  • Tetraaryl-1,2,3-triazolium salts were successfully synthesized and fully characterized.
  • High Gutmann-Beckett acidity numbers (up to 35.6) were recorded, indicating strong Lewis acidity.
  • The triazolium salts effectively catalyzed the hydrosilylation-deoxygenation of various substrates including ketones, aldehydes, acetals, alcohols, ethers, and silyl ethers.
  • Reactions proceeded under mild conditions with excellent yields.

Conclusions:

  • Tetraaryl-1,2,3-triazolium salts represent a novel class of highly effective nitrenium-based Lewis acid catalysts.
  • These findings establish triazolium ions as a promising Lewis acid platform for catalytic applications.
  • The developed catalysts offer a mild and efficient method for hydrosilylation-deoxygenation reactions.