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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.
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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 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
Preparation of Amides01:29

Preparation of Amides

3.2K
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...
3.2K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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

3.9K
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.
3.9K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

10.3K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
10.3K

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Two-component symmetrical diarylation of ynamides.

Aradhana Sahoo1, Shubham Dutta1, Akhila K Sahoo1

  • 1School of Chemistry, University of Hyderabad, Gachibowli, Hyderabad, Telangana, 500046, India. akhilchemistry12@gmail.com.

Organic & Biomolecular Chemistry
|July 3, 2023
PubMed
Summary
This summary is machine-generated.

This study introduces a new palladium-catalyzed method for diarylation of ynamides using aryl boronic acids. The efficient reaction occurs under mild conditions, offering a stereoselective route for synthesizing valuable organic compounds.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Ynamides are versatile synthetic intermediates.
  • Palladium-catalyzed cross-coupling reactions are crucial in organic synthesis.
  • Developing efficient methods for ynamide functionalization is an active research area.

Purpose of the Study:

  • To develop a novel palladium-catalyzed method for the dicarbofunctionalization of ynamides.
  • To achieve a two-component diarylation of ynamides with aryl boronic acids.
  • To establish a stereoselective and functional-group-tolerant synthetic route.

Main Methods:

  • Palladium-catalyzed reaction utilizing ynamides and aryl boronic acids.
  • Consecutive transmetalation mechanism involving a Pd(II)-complex.
  • Optimization of reaction conditions for mildness and broad substrate scope.
  • Control experiments to elucidate the reaction mechanism and role of the oxidant.

Main Results:

  • Successful dicarbofunctionalization of ynamides achieved.
  • High stereoselectivity observed in the diarylation process.
  • The reaction demonstrated tolerance to a wide array of functional groups.
  • Oxidant was confirmed to be essential for catalyst regeneration.

Conclusions:

  • A novel and efficient palladium-catalyzed diarylation of ynamides has been developed.
  • The method provides a stereoselective and functional-group-tolerant pathway.
  • This work expands the synthetic utility of ynamides in organic chemistry.