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

Limitations of Friedel–Crafts Reactions01:26

Limitations of Friedel–Crafts Reactions

4.6K
Several restrictions limit the use of Friedel–Crafts reactions. First, the halogen in the alkyl halide must be attached to an sp3-hybridized carbon for the Friedel–Crafts reactions to occur. Vinyl or aryl halides do not react since the carbocations formed are unstable under the reaction conditions. Second, Friedel–Crafts alkylation is susceptible to carbocation rearrangement, and the major products obtained have a rearranged carbon skeleton. In contrast, the acylium ion is...
4.6K
Electrophilic Aromatic Substitution: Friedel–Crafts Alkylation of Benzene01:17

Electrophilic Aromatic Substitution: Friedel–Crafts Alkylation of Benzene

5.7K
Friedel–Crafts reactions were developed in 1877 by the French chemist Charles Friedel and the American chemist James Crafts. Friedel–Crafts alkylation refers to the replacement of an aromatic proton with an alkyl group via electrophilic aromatic substitution. A Lewis acid catalyst such as aluminum chloride reacts with an alkyl halide to form a carbocation. The resulting carbocation then reacts with the aromatic ring and undergoes a series of electron rearrangements before giving the...
5.7K
Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene01:11

Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene

7.2K
The Friedel–Crafts acylation reactions involve the addition of an acyl group to an aromatic ring. These reactions proceed via electrophilic aromatic substitution by employing an acyl chloride and a Lewis acid catalyst such as aluminum chloride to form aryl ketone.
7.2K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

2.6K
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...
2.6K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

6.9K
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.
6.9K
Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

12.4K
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...
12.4K

You might also read

Related Articles

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

Sort by
Same author

Construction of a thiourea-functionalized metallomacrocycle for the reductive amination of furfural under mild conditions.

Dalton transactions (Cambridge, England : 2003)·2026
Same author

Efficient Light-Driven CO<sub>2</sub> Capture and Reversible Release Enabled by Metastable Photoacid-Decorated Metal-Organic Frameworks.

Journal of the American Chemical Society·2026
Same author

Manganese-based metal-organic frameworks with nickel porphyrin for highly selective photocatalytic oxidation of benzylic C(sp<sup>3</sup>)-H bonds.

Chemical communications (Cambridge, England)·2026
Same author

A dye-loaded Fe<sub>4</sub>L<sub>4</sub> cage for efficient photocatalytic C(sp<sup>3</sup>)-H activation.

Dalton transactions (Cambridge, England : 2003)·2026
Same author

Merging bioinspired incubation with supramolecular photocatalysis for Michaelis CO<sub>2</sub> reduction beyond enzymes.

Nature communications·2026
Same author

Glutathione-Mediated Biomimetic NO Activation with Coordination Capsules for NH<sub>3</sub> and α-Amino Acid Electrosynthesis.

Journal of the American Chemical Society·2026

Related Experiment Video

Updated: Apr 30, 2026

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs
08:25

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs

Published on: January 17, 2020

6.6K

Squaramide-functionalized coordination capsule as hydrogen-bond-donor catalyst for efficient Friedel-Crafts

Song Zhao1, Zhong Wei1, Yao Wang1

  • 1School of Chemistry, Dalian University of Technology, 116024, P. R. China. xjing@dlut.edu.cn.

Chemical Communications (Cambridge, England)
|April 29, 2026
PubMed
Summary

A novel squaramide-functionalized coordination capsule efficiently catalyzes Friedel-Crafts alkylation. Its unique structure activates substrates within a confined cavity, accelerating the reaction.

More Related Videos

Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes
12:08

Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes

Published on: June 24, 2022

3.4K
Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
09:37

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry

Published on: October 18, 2019

10.0K

Related Experiment Videos

Last Updated: Apr 30, 2026

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs
08:25

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs

Published on: January 17, 2020

6.6K
Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes
12:08

Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes

Published on: June 24, 2022

3.4K
Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
09:37

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry

Published on: October 18, 2019

10.0K

Area of Science:

  • Supramolecular Chemistry
  • Catalysis
  • Organic Synthesis

Background:

  • Friedel-Crafts alkylation is a fundamental organic reaction.
  • Developing efficient and selective catalysts remains a key challenge.
  • Supramolecular chemistry offers unique strategies for catalyst design.

Purpose of the Study:

  • To construct a tetranuclear coordination capsule functionalized with squaramide groups.
  • To investigate its efficacy as a catalyst for Friedel-Crafts alkylation.
  • To elucidate the mechanism of catalytic enhancement.

Main Methods:

  • Synthesis of a tetranuclear coordination capsule.
  • Functionalization with squaramide moieties.
  • Catalytic testing in Friedel-Crafts alkylation reactions.
  • Structural and mechanistic studies.

Main Results:

  • The squaramide-functionalized capsule demonstrated high catalytic efficiency.
  • The supramolecular architecture prevented catalyst self-association.
  • A confined, hydrogen-bonding-rich cavity facilitated substrate encapsulation and activation.
  • The catalyst accelerated the nucleophilic addition step.

Conclusions:

  • The designed coordination capsule is an effective catalyst for Friedel-Crafts alkylation.
  • The confined microenvironment and hydrogen-bonding interactions are crucial for catalytic activity.
  • This work highlights the potential of supramolecular capsules in catalysis.