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Related Concept Videos

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
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Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

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Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
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Preparation of Alkynes: Dehydrohalogenation02:34

Preparation of Alkynes: Dehydrohalogenation

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Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
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Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

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Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
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Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

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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...
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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Copper-Catalyzed Azidative Multifunctionalization of Alkynes.

Guangfan Zheng1, Jiaqiong Sun1, Yang Liu1

  • 1Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry, Northeast Normal University , Changchun 130024, China.

The Journal of Organic Chemistry
|October 28, 2017
PubMed
Summary

A new copper-catalyzed reaction efficiently converts alkynes into α-azido-α-aryl imines using N-fluorobenzenesulfonimide and trimethylsilyl azide. These products can be further transformed into valuable heterocyclic compounds.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Multifunctionalization of alkynes is crucial for synthesizing complex organic molecules.
  • Developing efficient and mild synthetic routes remains a key challenge in organic synthesis.

Purpose of the Study:

  • To develop a facile and efficient copper-catalyzed method for the azidative multifunctionalization of alkynes.
  • To synthesize α-azido-α-aryl imines from a wide range of alkynes in a single step.

Main Methods:

  • Copper-catalyzed reaction utilizing N-fluorobenzenesulfonimide (NFSI) as the nitrogen and aryl source.
  • Employing trimethylsilyl azide (TMSN3) as the azido source.
  • Performing the transformation under mild reaction conditions.

Main Results:

  • Successful development of a facile and efficient copper-catalyzed azidative multifunctionalization of alkynes.
  • Synthesis of various α-azido-α-aryl imines in good yields from diverse alkynes.
  • Demonstration of the conversion of the obtained imines into 1,5-piperizine-fused 1,2,3-triazoles and azido enamines.

Conclusions:

  • The developed method offers a straightforward and effective route to α-azido-α-aryl imines.
  • The synthesized imines serve as versatile intermediates for further chemical transformations.
  • This study expands the synthetic toolbox for accessing nitrogen-containing heterocycles.