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Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

2.7K
Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
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Preparation of Amines: Alkylation of Ammonia and Amines01:30

Preparation of Amines: Alkylation of Ammonia and Amines

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Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
3.8K
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

3.6K
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...
3.6K
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

2.6K
Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
2.6K
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
Aldehydes and Ketones with Amines: Enamine Formation Mechanism01:14

Aldehydes and Ketones with Amines: Enamine Formation Mechanism

6.5K
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...
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Related Experiment Video

Updated: Apr 21, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
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A robust and modular synthesis of ynamides.

Steven J Mansfield1, Craig D Campbell, Michael W Jones

  • 1Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, UK. edward.anderson@chem.ox.ac.uk.

Chemical Communications (Cambridge, England)
|November 7, 2014
PubMed
Summary

A new, versatile ynamide synthesis method is introduced using trichloroethene. This approach efficiently produces various ynamides, overcoming limitations of existing synthetic strategies.

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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
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Area of Science:

  • Organic Synthesis
  • Methodology Development

Background:

  • Ynamides are valuable synthetic intermediates.
  • Existing ynamide synthesis methods have limitations in scope and substrate compatibility.

Purpose of the Study:

  • To develop a flexible and modular synthesis for ynamides.
  • To utilize an inexpensive two-carbon synthon for ynamide formation.

Main Methods:

  • Employing trichloroethene as a two-carbon building block.
  • Reacting a wide range of amides and electrophiles.

Main Results:

  • Successful synthesis of diverse ynamides.
  • Demonstrated compatibility with challenging substrates like acyclic carbamates, hindered amides, and aryl amides.
  • Overcame limitations of previous ynamide synthesis approaches.

Conclusions:

  • The reported method provides a broadly applicable and efficient route to ynamides.
  • This strategy expands the accessibility of ynamide functionality in organic synthesis.