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

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

5.9K
Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
5.9K
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

2.2K
Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
2.2K
Reactions at the Benzylic Position: Halogenation01:11

Reactions at the Benzylic Position: Halogenation

2.5K
Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
2.5K
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
Electrophilic Aromatic Substitution: Friedel–Crafts Alkylation of Benzene01:17

Electrophilic Aromatic Substitution: Friedel–Crafts Alkylation of Benzene

6.5K
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...
6.5K
Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene01:11

Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene

7.0K
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.
7.0K

You might also read

Related Articles

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

Sort by
Same author

C(<i>sp</i><sup>3</sup>)-H Activation/Cleavage of Alcohols and C-C Coupling with Nonactivated Alkenes through Rhodium Catalysis Triggered by O<sub>2</sub>.

Organic letters·2026
Same author

Iron-mediated reactions of gem-dihaloalkanes with α,β-unsaturated carbonyl compounds.

Chemical science·2026
Same author

Accessing Dihydroazepines and Cyclopentanes from Enynyl Ketones.

Organic letters·2025
Same author

Development of Ir(III) Photocatalysts Enabling Blue-Light-Induced Hydrocarboxylation of Unactivated Alkenes and Arenes.

Organic letters·2025
Same author

Au<sub>6</sub>Cu<sub>2</sub> Clusters with High Electron Affinity and Oxygen-Mimetic Properties for Hypoxic Tumor Radiosensitization.

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

One-pot Nazarov cyclization/oxidative 1,2-carbon rearrangement/Ritter reaction to access 5-quaternary-4-amidocyclopent-2-enones and 2-quaternary-3-amidoindanones.

Chemical communications (Cambridge, England)·2025

Related Experiment Video

Updated: Jun 14, 2025

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of &#945;,&#946;-Unsaturated Compounds and Alkynes
05:34

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes

Published on: December 16, 2019

7.8K

Divergent Synthesis of Symmetric Benzenes and Fluorenones.

Yingjian Gong1, Li Li1, Qian Wu1

  • 1School of Chemistry and Chemical Engineering, Chongqing University, 174 Shazheng Street, Chongqing 400044, China.

Organic Letters
|June 12, 2025
PubMed
Summary
This summary is machine-generated.

Researchers developed a new divergent synthesis for benzene derivatives using a copper-catalyzed cycloaromatization. This method efficiently creates symmetrical aromatics and functionalized fluorenones from simple precursors.

More Related Videos

Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
10:10

Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes

Published on: July 28, 2018

6.4K
Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
08:43

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

10.2K

Related Experiment Videos

Last Updated: Jun 14, 2025

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of &#945;,&#946;-Unsaturated Compounds and Alkynes
05:34

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes

Published on: December 16, 2019

7.8K
Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
10:10

Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes

Published on: July 28, 2018

6.4K
Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
08:43

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

10.2K

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Benzene rings are crucial structural motifs in biologically active molecules and advanced materials.
  • Developing efficient synthetic routes for substituted benzene derivatives is essential for various scientific fields.

Purpose of the Study:

  • To present a novel divergent synthetic strategy for accessing 1,2-difuryl-substituted symmetrical benzene and functionalized fluorenones.
  • To establish an alternative method for synthesizing symmetrical aromatic compounds.

Main Methods:

  • A copper-mediated dimeric cycloaromatization cascade sequence was employed.
  • Readily available dienynyl ketones were used as starting materials.
  • The protocol facilitates the generation of aromatic cores.

Main Results:

  • The synthesis successfully yielded 1,2-difuryl-substituted symmetrical benzene derivatives.
  • Highly functionalized fluorenones were also accessed through this method.
  • The strategy provides a framework for oxidative transformation of furans.

Conclusions:

  • The presented copper-catalyzed cascade reaction offers an innovative approach to synthesizing complex aromatic structures.
  • This method expands the synthetic toolkit for creating valuable organic compounds from accessible precursors.