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Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

3.9K
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...
3.9K
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

2.9K
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
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
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

2.8K
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

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Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
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Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

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Click assembly through selective azaylide formation.

Mayo Hamada1, Gaku Orimoto1, Suguru Yoshida1

  • 1Department of Biological Science and Technology, Faculty of Advanced Engineering, Tokyo University of Science, 6-3-1 Niijuku, Katsushika-ku, Tokyo 125-8585, Japan. s-yoshida@rs.tus.ac.jp.

Chemical Communications (Cambridge, England)
|July 10, 2024
PubMed
Summary

A new trivalent platform enables efficient triple-click assembly. This method selectively forms azaylides, allowing rapid Staudinger and triazole reactions to create trifunctionalized molecules in just three steps.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Molecular Assembly

Background:

  • Click chemistry facilitates efficient molecular construction.
  • Selective functionalization of azides is crucial for complex molecule synthesis.
  • Triarylphosphine reagents offer versatile reactivity in organic transformations.

Purpose of the Study:

  • To develop an efficient triple-click assembly method.
  • To achieve selective azaylide formation using a novel trivalent platform.
  • To synthesize trifunctionalized molecules through a streamlined multi-step process.

Main Methods:

  • Design and synthesis of a novel trivalent platform.
  • Selective azaylide formation of 2,3,5,6-tetrafluorophenyl azides with o-ester-substituted triarylphosphines.
  • Sequential Staudinger reaction and triazole formation.

Main Results:

  • Demonstrated selective azaylide formation, leaving 2,6-dichlorophenyl azides unreacted.
  • Successfully performed rapid Staudinger reaction on the dichlorophenyl azides.
  • Achieved trifunctionalized molecule synthesis in a three-step sequence.

Conclusions:

  • The developed trivalent platform provides an efficient route for triple-click assembly.
  • Selective azide functionalization is a key feature of this methodology.
  • This approach offers a rapid and effective strategy for synthesizing complex trifunctionalized molecules.