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Related Concept Videos

Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

Aldehydes and Ketones with Amines: Imine Formation Mechanism

8.0K
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...
8.0K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.5K
Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
2.5K
Preparation of Amides01:29

Preparation of Amides

3.8K
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...
3.8K
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

4.0K
Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
4.0K
Amides to Carboxylic Acids: Hydrolysis01:28

Amides to Carboxylic Acids: Hydrolysis

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Amides can undergo either acid-catalyzed hydrolysis or base-promoted hydrolysis through a typical nucleophilic acyl substitution. Each hydrolysis requires severe conditions.
Acid-catalyzed hydrolysis:
Hydrolysis of amides under acidic conditions yields carboxylic acids. Since the reaction occurs slowly, hydrolysis requires the conditions of heat.
The mechanism begins with the protonation of the carbonyl oxygen by the acid catalyst. The protonation makes the amide carbonyl carbon more...
4.3K
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview01:16

Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview

6.1K
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.
6.1K

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Related Experiment Video

Updated: Jan 3, 2026

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
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Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization

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Visible Light-Induced Amide Bond Formation.

Wangze Song1, Kun Dong1, Ming Li1

  • 1State Key Laboratory of Fine Chemicals, School of Chemical Engineering , Dalian University of Technology , Dalian 116024 , P. R. China.

Organic Letters
|November 20, 2019
PubMed
Summary
This summary is machine-generated.

A novel green chemistry method enables metal-free amide bond formation using photoredox catalysis. This selective reaction offers high yields and broad applicability, including synthesizing key pharmaceutical compounds.

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Area of Science:

  • Organic Chemistry
  • Green Chemistry
  • Catalysis

Background:

  • Amide bond formation is crucial in organic synthesis, particularly for pharmaceuticals.
  • Traditional methods often require harsh conditions, metal catalysts, or stoichiometric reagents.
  • Developing sustainable and efficient amide synthesis remains a significant challenge.

Purpose of the Study:

  • To develop a metal-, base-, and additive-free amide bond formation reaction.
  • To utilize organic photoredox catalysis for a greener synthetic approach.
  • To demonstrate the functional group tolerance and broad applicability of the developed method.

Main Methods:

  • Employing an organic photoredox catalyst to facilitate amide bond formation.
  • Investigating the reaction's selectivity in the presence of various functional groups.
  • Testing a wide range of substrates to establish substrate scope.
  • Evaluating reaction performance under ambient air and aqueous conditions.

Main Results:

  • Achieved metal-, base-, and additive-free amide bond formation.
  • Demonstrated excellent functional group tolerance, preserving alcohols, phenols, ethers, esters, halogens, and heterocycles.
  • Obtained high yields, up to 95%, across a broad substrate scope.
  • Confirmed compatibility with air and water, highlighting the method's robustness.

Conclusions:

  • The developed photoredox-catalyzed reaction provides a green and efficient alternative for amide synthesis.
  • The method's high selectivity and functional group tolerance make it suitable for complex molecule synthesis.
  • The successful synthesis of drug molecules like paracetamol and melatonin underscores its practical utility in medicinal chemistry.