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Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

4.6K
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...
4.6K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

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

2.4K
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...
2.4K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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

4.8K
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.
4.8K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

3.3K
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.
3.3K
Preparation of Amides01:29

Preparation of Amides

3.9K
Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
3.9K
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

3.8K
Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction...
3.8K

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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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Cu-NHC azide complex: synthesis and reactivity.

Michael Trose1, Fady Nahra2, David B Cordes1

  • 1School of Chemistry, University of St Andrews, St Andrews, KY16 9ST, UK.

Chemical Communications (Cambridge, England)
|September 20, 2019
PubMed
Summary
This summary is machine-generated.

Researchers synthesized the first N-heterocyclic carbene (NHC)-based copper azide complex. This novel compound

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The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
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Area of Science:

  • Inorganic Chemistry
  • Organometallic Chemistry

Background:

  • N-heterocyclic carbenes (NHCs) are versatile ligands in organometallic chemistry.
  • Copper azide complexes have applications in various chemical transformations.

Purpose of the Study:

  • To report the first synthesis of an NHC-copper azide complex.
  • To investigate the reactivity and synthetic utility of this new complex.

Main Methods:

  • Synthesis of the NHC-copper azide complex.
  • Reactions with various electrophilic and nucleophilic reagents.
  • Characterization of new complexes using spectroscopic techniques.

Main Results:

  • Successful synthesis of the first NHC-copper azide complex.
  • Generation of 8 new copper complexes through reactivity studies.
  • Demonstration of the complex's utility in synthesizing diverse copper compounds.

Conclusions:

  • The reported NHC-copper azide complex is a valuable precursor for novel copper compounds.
  • This work expands the scope of NHC-ligated copper chemistry.
  • The reactivity studies highlight the potential of this complex in synthetic applications.