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Related Concept Videos

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
Amides to Carboxylic Acids: Hydrolysis01:28

Amides to Carboxylic Acids: Hydrolysis

4.5K
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...
4.5K
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

3.5K
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...
3.5K
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

4.4K
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...
4.4K
Amides to Amines: LiAlH4 Reduction01:20

Amides to Amines: LiAlH4 Reduction

6.3K
Amide reduction with strong reducing agents like lithium aluminum hydride proceeds through a nucleophilic acyl substitution to form amines. Primary, secondary, and tertiary amides yield primary, secondary, and tertiary amines, respectively.
Amide reduction requires two equivalents of the reducing agent, acting as a source of hydride ions. As shown in the figure, the reaction is initiated with a nucleophilic attack by the hydride ion at the carbonyl carbon to form a tetrahedral intermediate.
6.3K
Preparation of Amines: Reduction of Amides and Nitriles01:13

Preparation of Amines: Reduction of Amides and Nitriles

3.1K
Nitriles can be reduced to primary amines using reducing agents like lithium aluminum hydride or catalytic hydrogenation. The reduction introduces an amino group with an extra carbon in the skeleton. Nitriles are formed from the reaction between alkyl halides and sodium cyanide through the SN2 mechanism. Primary alkyl halides are the preferred substrates to prepare nitriles.
Amides can be reduced to primary, secondary, and tertiary amines using catalytic hydrogenation, active metals like Fe,...
3.1K

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A Practical and General Amidation Method from Isocyanates Enabled by Flow Technology.

Jason D Williams1,2, William J Kerr1, Stuart G Leach2

  • 1Department of Pure and Applied Chemistry, WestCHEM, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, UK.

Angewandte Chemie (International Ed. in English)
|July 19, 2018
PubMed
Summary
This summary is machine-generated.

Researchers developed a new method for synthesizing amides using Grignard reagents and isocyanates. This efficient and scalable process offers broad substrate tolerance, overcoming limitations of previous amide synthesis techniques.

Keywords:
C−C couplingGrignard reactionamidesflow chemistrysynthetic methods

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Amide synthesis is crucial in organic chemistry.
  • Traditional methods using carbon nucleophiles and isocyanates are limited by substrate scope and reaction conditions.

Purpose of the Study:

  • To develop a more efficient, scalable, and broadly applicable method for amide synthesis.
  • To overcome the limitations of existing carbon nucleophile-isocyanate reactions.

Main Methods:

  • Utilized Grignard reagents as carbon nucleophiles.
  • Employed isocyanates as electrophilic partners.
  • Applied flow chemistry techniques.
  • Used substoichiometric amounts of copper(II) bromide (CuBr2) as a catalyst.

Main Results:

  • Achieved high yields in amide formation.
  • Demonstrated excellent mass efficiency and scalability.
  • Showcased significant functional group tolerance.
  • Successfully reacted substrates previously incompatible with other methods.

Conclusions:

  • The developed method provides a robust and versatile route to amides.
  • Flow chemistry and CuBr2 catalysis enable a broader substrate scope than previously possible.
  • This approach enhances the utility of Grignard reagents in amide synthesis.