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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...
2.9K
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
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

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

Diazonium Group Substitution: –OH and –H

2.7K
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.
2.7K
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview01:27

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

1.7K
Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
1.7K
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

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

3.0K
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...
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Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
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Dehydrogenative Coupling Reactions with Guanidino-Functionalized Aromatics.

Petra Walter1, Maximilian Schulz1, Olaf Hübner1

  • 1Inorganic Chemistry, Ruprecht-Karls Universität Heidelberg, Im Neuenheimer Feld 270, Heidelberg, 69120, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|October 7, 2024
PubMed
Summary

Researchers developed novel guanidino-functionalized aromatic molecules (GFAs) for efficient dehydrogenative coupling reactions. These GFAs facilitate the formation of new carbon-element bonds, advancing synthetic organic chemistry.

Keywords:
dehydrogenative coupling reactionsguanidinesoxidative couplingproton-coupled electron transferredox-acive molecules

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Area of Science:

  • Synthetic organic chemistry
  • Organometallic chemistry

Background:

  • Dehydrogenative coupling (DC) reactions are crucial for forming carbon-element bonds.
  • Developing efficient reagents for DC reactions remains a key challenge in organic synthesis.

Purpose of the Study:

  • To synthesize and characterize novel redox-active guanidino-functionalized aromatic molecules (GFAs).
  • To evaluate the performance of these GFAs in various dehydrogenative coupling reactions, including C-C and C-O bond formation.

Main Methods:

  • Synthesis and comprehensive characterization of GFAs in multiple redox and protonation states.
  • Comparative analysis of GFA performance in proton-coupled electron transfer (PCET) reactions.
  • Application of GFAs in four distinct DC reactions with varying mechanisms.

Main Results:

  • Successful synthesis and characterization of new redox-active GFAs.
  • Demonstrated utility of GFAs in facilitating C-C and C-O bond formation via DC reactions.
  • Comparative performance data highlighting the effectiveness of GFAs in PCET and DC reactions.

Conclusions:

  • Novel GFAs are effective reagents for dehydrogenative coupling reactions.
  • The characterized GFAs offer versatile applications in constructing carbon-element bonds.
  • This work provides a foundation for further development of GFA-based catalytic systems.