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: Overview01:16

Electrophilic Aromatic Substitution: Overview

10.9K
In an electrophilic aromatic substitution reaction, an electrophile substitutes for a hydrogen of an aromatic compound.
10.9K
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

3.8K
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...
3.8K
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: 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
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
Radical Formation: Elimination00:51

Radical Formation: Elimination

1.7K
Another method of radical formation is the elimination process. It is the opposite of the addition route and is driven by the instability of the radical. For example, as depicted in Figure 1, dibenzoyl peroxide yields a pair of unstable radicals upon homolysis. Given its instability, this radical spontaneously undergoes elimination via a C–C bond cleavage to form a relatively more stable phenyl radical. The mechanism involves cleavage of the bond between the α and β positions...
1.7K

You might also read

Related Articles

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

Sort by
Same author

A Mild Protocol for Highly Congested and Functionalized C(sp<sup>3</sup>)-N Bonds Construction.

The Journal of organic chemistry·2026
Same author

Dehydrogenative Cyclization of 2-Aminobenzyl Alcohols with Ketones or Secondary Alcohols to Construct Quinolines.

The Journal of organic chemistry·2025
Same author

Transition-Metal-Free Synthesis of Indolo[2,1-<i>a</i>]isoquinolines via Intramolecular Tandem Radical Cyclization.

The Journal of organic chemistry·2025
Same author

Visible Light-Induced Synthesis of Sulfenamides via Oxidative Coupling of Amines with Thiols.

Organic letters·2025
Same author

N-Heterocyclic Carbene Catalysis for Polycyclic Benzazepines Assembly: Regioselective Intramolecular Tandem Radical Cyclization.

Organic letters·2024
Same author

Construction of Functionalized Oxindoles by Quinone-Carbonate Synergistically Triggered Intermolecular Radical Coupling.

The Journal of organic chemistry·2024
Same journal

Nickel-Catalyzed 1,2-Distyrylation of 3-Buten-1-ol.

Organic letters·2026
Same journal

Correction to "Engineering Ene-Reductases for the Chemoenzymatic Synthesis of a Sacubitril Intermediate and Its Derivatives".

Organic letters·2026
Same journal

Synthesis of Thieno[3,2-<i>b</i>]thiophene-Cored Hexacyclic Molecules Via the Pictet-Spengler Reaction.

Organic letters·2026
Same journal

Synthesis of N-BOH Benzazaborines via a Modular GBB-Based Strategy.

Organic letters·2026
Same journal

Nickel-Catalyzed 8-Endo Cyclization/Carbonylation for the Synthesis of Eight-Membered Lactams.

Organic letters·2026
Same journal

The Exploration of TPhos as a Monodentate P-Ligand for Palladium-Catalyzed Regioselective Hydrothiocarbonylation of Styrenes under Neutral Conditions.

Organic letters·2026
See all related articles

Related Experiment Video

Updated: Jun 14, 2025

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
06:49

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst

Published on: April 22, 2016

11.8K

Defunctionalization Enabled by Intramolecular Radical Aromatic Ipso Substitution.

Qijing Zhang1, Tinglan Liu1, Lili Wu1

  • 1College of Chemistry and Materials Science, Jinan University, Guangzhou, Guangdong 511443, China.

Organic Letters
|September 5, 2024
PubMed
Summary
This summary is machine-generated.

A new copper-promoted method rapidly builds N-polyheterocycles through a chemoselective and regioselective defunctionalization process. Mechanistic studies suggest a single-electron transfer radical pathway may be involved in this synthesis.

More Related Videos

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
06:34

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Published on: June 20, 2014

13.8K
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

Related Experiment Videos

Last Updated: Jun 14, 2025

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
06:49

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst

Published on: April 22, 2016

11.8K
Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
06:34

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Published on: June 20, 2014

13.8K
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

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • N-polyheterocycles are important scaffolds in medicinal chemistry.
  • Efficient synthetic routes to N-polyheterocycles are crucial for drug discovery.

Purpose of the Study:

  • To develop a novel chemoselective and regioselective method for synthesizing N-polyheterocycles.
  • To investigate the mechanism of the developed synthetic procedure.

Main Methods:

  • Copper-promoted defunctionalization reaction.
  • Synthesis of various N-polyheterocycles.
  • Mechanistic studies involving radical processes.

Main Results:

  • A rapid and efficient procedure for constructing N-polyheterocycles was established.
  • The reaction proceeds with high chemoselectivity and regioselectivity.
  • Initial mechanistic investigations suggest a single-electron transfer radical pathway.

Conclusions:

  • The developed copper-promoted defunctionalization offers a powerful tool for N-polyheterocycle synthesis.
  • The findings provide insights into the reaction mechanism, potentially involving radical intermediates.