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

Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

4.0K
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
4.0K
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

3.7K
Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
3.7K
Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

9.9K
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.
9.9K
Electrophilic Aromatic Substitution: Overview01:16

Electrophilic Aromatic Substitution: Overview

10.7K
In an electrophilic aromatic substitution reaction, an electrophile substitutes for a hydrogen of an aromatic compound.
10.7K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.1K
Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
2.1K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

7.6K
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.
7.6K

You might also read

Related Articles

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

Sort by
Same author

Organocatalyzed Enantioselective Synthesis of Aryl-Substituted 4-Hydroxycyclopent-2-enones.

Organic letters·2026
Same author

Ruthenium-Catalyzed Acyloin Isomerization via Borrowing Hydrogen.

The Journal of organic chemistry·2026
Same author

Ruthenium-Catalyzed Diversified Kinetic Resolutions of Diaryl-Substituted Cyclobutenones via Asymmetric Transfer Hydrogenation.

Angewandte Chemie (International ed. in English)·2025
Same author

Copper-Catalyzed Dienylation of Aldehydes Using Propargylic Carbonates.

Organic letters·2025
Same author

Correction to "Catalytic Asymmetric Transfer Hydrogenation of Acylboronates: BMIDA as the Privileged Directing Group".

Journal of the American Chemical Society·2025
Same author

Copper-Catalyzed Asymmetric Nucleophilic Opening of 1,1,2,2-Tetrasubstituted Donor-Acceptor Cyclopropanes for the Synthesis of α-Tertiary Amines.

Journal of the American Chemical Society·2024
Same journal

The role of spacer length and flexibility in peptide self-assembly.

Beilstein journal of organic chemistry·2026
Same journal

Novel macrocycles: from synthesis to supramolecular function.

Beilstein journal of organic chemistry·2026
Same journal

Electrochemical reduction of unsaturated carbon-carbon bonds via 3d transition-metal catalysis.

Beilstein journal of organic chemistry·2026
Same journal

Synthesis of sterically shielded piperidine nitroxides via acid-catalyzed heterocyclization of β-aminoketone derivatives with ketones.

Beilstein journal of organic chemistry·2026
Same journal

Chiral cyclopropenimine-catalyzed enantioselective Michael reactions of phenol and benzofuran-derived α,β-unsaturated pyrazolamides with benzophenone-imine of glycine esters.

Beilstein journal of organic chemistry·2026
Same journal

A practical CO<sub>2</sub>-mediated synthesis of 5,6-carboxylated silicon-rhodamines for targeted probe development.

Beilstein journal of organic chemistry·2026
See all related articles

Related Experiment Video

Updated: Jun 8, 2025

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
09:58

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

Published on: February 24, 2015

11.2K

Copper-catalyzed yne-allylic substitutions: concept and recent developments.

Shuang Yang1, Xinqiang Fang1

  • 1State Key Laboratory of Structural Chemistry, and Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Center for Excellence in Molecular Synthesis, Fujian Institute of Research on the Structure of Matter, University of Chinese Academy of Sciences, Fuzhou 350100, China.

Beilstein Journal of Organic Chemistry
|November 5, 2024
PubMed
Summary
This summary is machine-generated.

Copper-catalyzed allylation and propargylation reactions create chiral alkenes and alkynes. Recent advances in yne-allylic substitution, using copper vinyl allenylidene intermediates, offer expanded synthetic possibilities and control over selectivity.

Keywords:
1,3-enyne1,4-enynecopper vinyl allenylidene intermediatecopper-catalysisyne-allylic substitution

More Related Videos

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

7.4K
Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

2.7K

Related Experiment Videos

Last Updated: Jun 8, 2025

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
09:58

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

Published on: February 24, 2015

11.2K
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

7.4K
Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

2.7K

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Asymmetric Synthesis

Background:

  • Catalytic allylation and propargylation are key for synthesizing enantioenriched α-chiral alkenes and alkynes.
  • Combining these reactions expands transition metal-catalyzed substitution.
  • Copper-catalyzed yne-allylic substitution, discovered in 2022, has rapidly advanced.

Purpose of the Study:

  • To review recent developments in copper-catalyzed yne-allylic substitution.
  • To illustrate the influence of reaction parameters on selectivity.
  • To highlight the utility of copper vinyl allenylidene intermediates.

Main Methods:

  • Review of literature on copper-catalyzed allylic and propargylic substitutions.
  • Analysis of regioselectivity and stereoselectivity in yne-allylic substitution reactions.
  • Discussion of the role of copper salts, ligands, and substrate substitution patterns.

Main Results:

  • Copper-catalyzed yne-allylic substitution has seen significant progress since 2022.
  • Key copper vinyl allenylidene intermediates are crucial for these transformations.
  • Regioselectivity and stereoselectivity are influenced by copper source, ligand, and substrate.

Conclusions:

  • Copper-catalyzed yne-allylic substitution is a powerful and developing synthetic strategy.
  • Understanding the interplay of catalyst, ligand, and substrate is key to controlling outcomes.
  • This methodology provides access to valuable chiral alkenes and alkynes.