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Related Concept Videos

Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

12.5K
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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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

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The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
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Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia02:10

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

10.8K
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, such as sodium,...
10.8K
Preparation of Alkynes: Dehydrohalogenation02:34

Preparation of Alkynes: Dehydrohalogenation

18.6K
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.
18.6K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

9.3K
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.
9.3K
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

2.3K
Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
2.3K

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Updated: Mar 21, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

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Toward vanadium-mediated alkyne metathesis.

Shirley Hernandez1, Vasilisa Krivovicheva1, Adenilson Sousa-Silva2

  • 1Department of Chemistry and Biochemistry, Florida International University Miami FL 33199 USA kbukhrya@fiu.edu.

Chemical Science
|March 20, 2026
PubMed
Summary
This summary is machine-generated.

Researchers explored vanadium-mediated alkyne metathesis, a sustainable alternative to current methods. They demonstrated key reaction steps and synthesized essential vanadium alkylidynes for future catalyst development.

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Sustainable Chemistry

Background:

  • Alkyne metathesis is crucial for synthesizing molecules with carbon-carbon triple bonds.
  • Current alkyne metathesis relies on expensive and potentially toxic second and third-row transition metals.
  • Developing first-row metal catalysts offers enhanced sustainability and cost-effectiveness.

Purpose of the Study:

  • To investigate the feasibility of vanadium-mediated alkyne metathesis.
  • To establish vanadium alkylidynes as key intermediates in this transformation.
  • To lay the foundation for novel catalytic systems using earth-abundant metals.

Main Methods:

  • Synthesis and characterization of novel vanadium alkylidynes.
  • Experimental studies on the reaction of vanadium alkylidynes with various alkynes.
  • Computational modeling to elucidate reaction mechanisms and intermediates.

Main Results:

  • Vanadium alkylidynes were successfully synthesized and characterized.
  • Demonstrated the formation of metallacyclobutadienes from the reaction of V alkylidynes with alkynes.
  • Computational studies confirmed the feasibility of the cycloreversion step for alkyne metathesis.

Conclusions:

  • Vanadium-mediated alkyne metathesis is a viable transformation.
  • Vanadium alkylidynes are critical intermediates for this process.
  • This work provides a foundation for developing sustainable alkyne metathesis catalysts based on first-row transition metals.