Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

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

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

8.0K
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.
8.0K
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

1.9K
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.
1.9K
¹H NMR: Long-Range Coupling01:27

¹H NMR: Long-Range Coupling

1.9K
The coupling interactions of nuclei across four or more bonds are usually weak, with J values less than 1 Hz. While these are usually not observed in spectra, the presence of multiple bonds along the coupling pathway can result in observable long-range coupling.
In alkenes, spin information is communicated via σ–π overlap, as seen in allylic (four-bond) and homoallylic (five-bond) couplings. These coupling interactions are stronger when the σ bond is parallel to the alkene...
1.9K
Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

10.5K
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.
10.5K
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

8.5K
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.
8.5K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

10.4K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
10.4K

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

The Reactivity of Diiron(I) Bis-cyclopentadienyl Tricarbonyl Aminocarbyne Complexes in Aqueous Media: A Case Study for Iron-Based Anticancer Agents.

Inorganic chemistry·2026
Same author

Revisiting the Crystal Structure of Metal-Organic Framework UTSA-16 for Chemical Consistency.

ACS organic & inorganic Au·2026
Same author

Selective Functionalization with Organophosphite Ligands of Atomically Precise Platinum Chini Clusters.

Inorganic chemistry·2026
Same author

Diiron(I) Bis(cyclopentadienyl) Complexes with Bridging Iminium Ligands: From Foundational Organometallic Chemistry to Unique Reactivity and Biological Potential.

Accounts of chemical research·2026
Same author

Isocyanide Incorporation Expands the Anticancer Potential of Diiron(I) Aminocarbyne Complexes.

Chemistry (Weinheim an der Bergstrasse, Germany)·2026
Same author

Ferrocene-Diiron(I) Bis(cyclopentadienyl) Conjugates Exhibit Potent In Vitro Cytotoxicity and Selectivity toward Cancer Cells Associated with ROS Scavenging.

Journal of medicinal chemistry·2026

Related Experiment Video

Updated: Aug 27, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

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

Published on: June 21, 2017

7.5K

Alkyne-alkenyl coupling at a diruthenium complex.

Giulio Bresciani1, Serena Boni1, Stefano Zacchini2

  • 1University of Pisa, Department of Chemistry and Industrial Chemistry, Via G. Moruzzi 13, I-56124 Pisa, Italy. fabio.marchetti1974@unipi.it.

Dalton Transactions (Cambridge, England : 2003)
|September 30, 2022
PubMed
Summary

This study explores the reactivity of bridging alkenyl ligands on diruthenium scaffolds with alkynes. Researchers discovered two distinct coupling outcomes, forming either ruthenacyclopentene or butadienyl complexes, with DFT calculations explaining product stability.

More Related Videos

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
10:51

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

Published on: April 10, 2015

12.2K
Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
11:44

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

Published on: March 20, 2014

25.5K

Related Experiment Videos

Last Updated: Aug 27, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

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

Published on: June 21, 2017

7.5K
The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
10:51

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

Published on: April 10, 2015

12.2K
Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
11:44

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

Published on: March 20, 2014

25.5K

Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Synthetic Chemistry

Background:

  • Dimetallic complexes serve as platforms for small molecule assembly.
  • Reactivity of bridging alkenyl ligands is key for modeling C-C bond formation.

Purpose of the Study:

  • Investigate the coupling of a bridging alkenyl ligand on a diruthenium scaffold with various alkynes.
  • Determine the factors influencing the reaction outcomes and product stability.

Main Methods:

  • Synthesis of a diruthenium complex with a bridging alkenyl ligand.
  • Reaction of the diruthenium complex with different alkynes under silver salt promotion.
  • Characterization of products using IR, NMR spectroscopy, and single crystal X-ray diffraction.
  • Computational analysis using Density Functional Theory (DFT) calculations.

Main Results:

  • Two distinct coupling pathways were observed: formation of a ruthenacyclopentene-based hydrocarbyl ligand or butadienyl complexes.
  • The nature of the alkyne substituent influenced the reaction outcome.
  • DFT calculations indicated greater stability for butadienyl complexes compared to ruthenacyclopentene isomers.
  • H-migration was identified as a key step, disfavored by carboxylato substituents on the alkyne.

Conclusions:

  • The diruthenium scaffold exhibits versatile reactivity with alkynes, leading to diverse organometallic structures.
  • Product distribution is governed by kinetic and thermodynamic factors, influenced by alkyne substituents.
  • Computational modeling provides insights into reaction mechanisms and relative product stabilities.