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Related Concept Videos

Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

Aldehydes and Ketones with Amines: Imine Formation Mechanism

8.7K
Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
8.7K
Preparation of Amides01:29

Preparation of Amides

4.1K
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...
4.1K
Aldehydes and Ketones with Amines: Enamine Formation Mechanism01:14

Aldehydes and Ketones with Amines: Enamine Formation Mechanism

8.0K
Enamine formation involves the addition of carbonyl compounds to a secondary amine through a series of reactions. The mechanism begins with the generation of carbinolamine, a nucleophilic attack followed by several proton transfer reactions. The hydroxyl group of the carbinolamine is converted into water to make a better leaving group that can push the reaction forward by eliminating a water molecule. In enamine formation, the last step involves the abstraction of a proton from the α carbon to...
8.0K
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview01:16

Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview

6.9K
Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named Schiff bases after its discoverer—the German chemist Hugo Schiff. On the other hand, secondary amines react with carbonyl compounds to give enamines. In enamines, the presence of a C=C double bond adjacent to the nitrogen atom leads to the delocalization of the lone pair.
6.9K
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

3.7K
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 para...
3.7K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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

5.0K
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.
5.0K

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Developing Photosensitizer-Cobaloxime Hybrids for Solar-Driven H2 Production in Aqueous Aerobic Conditions
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Sunlight assisted direct amide formation via a charge-transfer complex.

Irit Cohen1, Abhaya K Mishra, Galit Parvari

  • 1Schulich Faculty of Chemistry, Technion - Israel Institute of Technology, 3200008 Haifa, Israel.

Chemical Communications (Cambridge, England)
|August 26, 2017
PubMed
Summary

Novel charge-transfer complexes activate amines for mild, metal-free photochemical reactions using visible light. This method enables efficient dealkylative amide formation and gram-scale synthesis due to deep light penetration.

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Area of Science:

  • Organic Chemistry
  • Photochemistry
  • Synthetic Methodology

Background:

  • Amine activation is crucial for various synthetic transformations.
  • Traditional methods often require harsh conditions or transition metal catalysts.
  • Developing mild and efficient catalytic systems remains a key challenge in organic synthesis.

Purpose of the Study:

  • To introduce a novel method for activating amines using charge-transfer complexes.
  • To demonstrate a mild, transition metal-free, visible-light-mediated dealkylative amide formation.
  • To establish a scalable synthetic route for amide synthesis.

Main Methods:

  • Formation of charge-transfer complexes between amines and carbon tetrachloride.
  • Utilizing these complexes to activate amines for photochemical reactions.
  • Employing visible light irradiation to drive dealkylative amide formation from carboxylic acids and amines.

Main Results:

  • Successful activation of amines via charge-transfer complexation.
  • Mild and efficient dealkylative amide formation under visible light.
  • Demonstration of gram-scale synthesis enabled by the low absorption coefficient of the complex, allowing deep light penetration.

Conclusions:

  • Charge-transfer complexes offer a novel strategy for amine activation in photochemistry.
  • The developed method provides a mild, metal-free, and scalable approach to amide synthesis.
  • This work expands the toolkit for visible-light photoredox catalysis in organic synthesis.