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Related Concept Videos

Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

3.2K
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...
3.2K
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

2.8K
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
2.8K
Amides to Carboxylic Acids: Hydrolysis01:28

Amides to Carboxylic Acids: Hydrolysis

3.6K
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...
3.6K
Preparation of Amides01:29

Preparation of Amides

3.3K
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...
3.3K
Amines to Alkenes: Cope Elimination01:14

Amines to Alkenes: Cope Elimination

2.1K
Cope elimination reaction involves the conversion of tertiary amines to alkene using hydrogen peroxide under thermal conditions, as depicted in figure 1.
2.1K
Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia02:10

Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia

9.7K
Alkynes can be reduced to trans-alkenes using sodium or lithium in liquid ammonia. The reaction, known as dissolving metal reduction, proceeds with an anti addition of hydrogen across the carbon–carbon triple bond to form the trans product. Since ammonia exists as a gas (bp = −33°C) at room temperature, the reaction is carried out at low temperatures using a mixture of dry ice (sublimes at −78°C) and acetone. 
When dissolved in liquid ammonia, an alkali metal,...
9.7K

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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
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A CO2-Catalyzed Transamidation Reaction.

Yang Yang1, Jian Liu1, Fadhil S Kamounah1

  • 1Department of Chemistry, University of Copenhagen, Universitetsparken 5, Copenhagen Ø 2100, Denmark.

The Journal of Organic Chemistry
|November 1, 2021
PubMed
Summary
This summary is machine-generated.

Carbon dioxide (CO2) acts as a traceless catalyst, accelerating transamidation reactions with various amide donors and amine nucleophiles. This discovery offers new possibilities for peptide modification and polymer degradation.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Green Chemistry

Background:

  • Transamidation reactions typically require harsh conditions, including excess reagents or transition metal catalysts.
  • Developing milder and more efficient catalytic systems for transamidation is crucial for sustainable chemical synthesis.

Purpose of the Study:

  • To investigate the potential of carbon dioxide (CO2) as a traceless catalyst for transamidation reactions.
  • To explore the scope and limitations of CO2-catalyzed transamidation with diverse amide donors and nucleophiles.
  • To elucidate the catalytic mechanism of CO2 in transamidation.

Main Methods:

  • Utilized catalytic amounts of CO2 to mediate transamidation reactions.
  • Tested a range of primary, secondary, and tertiary amide donors and various amine nucleophiles, including amino acid derivatives.
  • Performed comparative studies under N2 atmosphere, Hammett studies, kinetic analysis, and Density Functional Theory (DFT) calculations.

Main Results:

  • CO2 significantly accelerated transamidation reactions with various amide donors.
  • The catalytic system tolerated diverse amine nucleophiles, enabling peptide modification and polymer degradation (e.g., Nylon-6,6).
  • Weinreb amides showed distinct reactivity under CO2 catalysis, and DFT calculations supported CO2's role in stabilizing tetrahedral intermediates.

Conclusions:

  • CO2 can serve as an effective and traceless catalyst for transamidation reactions.
  • The catalytic mechanism involves the stabilization of tetrahedral intermediates through covalent binding with electrophilic CO2.
  • This approach provides a greener and more efficient alternative for amide bond transformations.