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

8.2K
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.
8.2K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.5K
Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
3.5K
α-Alkylation of Ketones via Enolate Ions01:10

α-Alkylation of Ketones via Enolate Ions

3.3K
Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
3.3K
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

4.1K
By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
4.1K
Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

12.7K
Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...
12.7K
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

2.0K
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.
2.0K

You might also read

Related Articles

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

Sort by
Same author

PharmaGNN: a model for odor prediction based on graph neural networks.

Journal of the science of food and agriculture·2026
Same author

Sulfur Vacancy-Engineered 2D/2D ZnIn<sub>2</sub>S<sub>4</sub>/Zn-TCPP S-Scheme Heterojunction for Efficient Photocatalytic H<sub>2</sub>O<sub>2</sub> Production.

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

Stereodivergent Synthesis of Allylic Phosphonates.

The Journal of organic chemistry·2026
Same author

Fluoride-Initiated Annulation of Alkynoates and Trifluoromethyl Alkenes.

Organic letters·2026
Same author

Organocatalytic atom transfer radical polymerization with light and pH dual-gated regulation.

Nature communications·2026
Same author

Construction of a Cd<sub>6</sub>Eu<sub>4</sub>-containing coordination polymer for luminescence detection of ketoprofen as an anti-inflammatory drug.

Chemical communications (Cambridge, England)·2026

Related Experiment Video

Updated: Oct 4, 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

Electrocatalytic Allylic C-H Alkylation Enabled by a Dual-Function Cobalt Catalyst.

Ming Chen1, Zheng-Jian Wu1, Jinshuai Song2

  • 1State Key Laboratory of Physical Chemistry of Solid Surfaces, Innovative Collaboration Center of Chemistry for Energy Materials, Key Laboratory of Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China.

Angewandte Chemie (International Ed. in English)
|February 7, 2022
PubMed
Summary

This study introduces an electrocatalytic method for direct allylic C-H bond alkylation using a cobalt catalyst. This approach enables efficient synthesis of valuable alkenyl products from simple alkenes without pre-functionalization.

Keywords:
AlkenesCobaltElectrocatalysisOxidationRadicals

More Related Videos

Synthesis of Metal Nanoparticles Supported on Carbon Nanotube with Doped Co and N Atoms and its Catalytic Applications in Hydrogen Production
08:40

Synthesis of Metal Nanoparticles Supported on Carbon Nanotube with Doped Co and N Atoms and its Catalytic Applications in Hydrogen Production

Published on: December 6, 2021

3.8K
Synthesis and Performance Characterizations of Transition Metal Single Atom Catalyst for Electrochemical CO2 Reduction
10:57

Synthesis and Performance Characterizations of Transition Metal Single Atom Catalyst for Electrochemical CO2 Reduction

Published on: April 10, 2018

18.5K

Related Experiment Videos

Last Updated: Oct 4, 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
Synthesis of Metal Nanoparticles Supported on Carbon Nanotube with Doped Co and N Atoms and its Catalytic Applications in Hydrogen Production
08:40

Synthesis of Metal Nanoparticles Supported on Carbon Nanotube with Doped Co and N Atoms and its Catalytic Applications in Hydrogen Production

Published on: December 6, 2021

3.8K
Synthesis and Performance Characterizations of Transition Metal Single Atom Catalyst for Electrochemical CO2 Reduction
10:57

Synthesis and Performance Characterizations of Transition Metal Single Atom Catalyst for Electrochemical CO2 Reduction

Published on: April 10, 2018

18.5K

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Electrochemistry

Background:

  • Direct functionalization of C-H bonds is a key strategy in organic synthesis, reducing steps and waste.
  • Allylic C-H functionalization offers a pathway to valuable alkenyl-substituted compounds.
  • Existing methods often require pre-functionalized substrates or harsh conditions.

Purpose of the Study:

  • To develop an efficient and mild electrocatalytic method for the direct alkylation of allylic C-H bonds.
  • To utilize a readily available cobalt-salen complex as a molecular catalyst for this transformation.
  • To demonstrate the broad substrate scope and synthetic utility of the developed method.

Main Methods:

  • Electrocatalytic allylic C-H alkylation using a cobalt-salen catalyst.
  • Employing carbon nucleophiles for C(sp3)-H/C(sp3)-H cross-coupling.
  • Utilizing H2 evolution as the driving force, eliminating the need for external oxidants.

Main Results:

  • Achieved direct allylic C-H alkylation with carbon nucleophiles under mild electrochemical conditions.
  • Demonstrated excellent functional group tolerance and compatibility with diverse linear and branched terminal alkenes.
  • Validated scalability up to 200 mmol with low catalyst loading and electrolyte concentration.

Conclusions:

  • The developed electrocatalytic method provides a sustainable and efficient route for allylic C-H functionalization.
  • The cobalt-catalyzed radical process offers a unique advantage for late-stage functionalization of complex molecules.
  • This approach minimizes pre-functionalization steps, aligning with green chemistry principles.