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

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.
Halogenation of Alkenes02:46

Halogenation of Alkenes

Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

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

Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene

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.
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism01:13

Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism

Carboxylic acids react with alcohols to yield esters via an acid-catalyzed condensation reaction called Fischer esterification. This is a nucleophilic acyl substitution reaction that proceeds via a tetrahedral intermediate, where a water molecule is eliminated as the leaving group.

You might also read

Related Articles

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

Sort by
Same author

NF<sub>3</sub> for difluoroamination of tertiary lithium reagents.

Organic & biomolecular chemistry·2026
Same author

Hydroxyl proton transfer for the deoxygenative reduction of alcohols mediated by Ph<sub>3</sub>P/ICH<sub>2</sub>CH<sub>2</sub>I.

Chemical communications (Cambridge, England)·2026
Same author

Photocatalytic Transfer of Trifluoromethylcarbenes for X-H Insertion, Oxetane Skeleton Editing, and Alkene Cyclopropanation.

Organic letters·2026
Same author

Branched Fluoroether Ethyl Surfactants as Multi-Stage Degradable Platforms for Addressing the PFAS Dilemma.

Environmental science & technology·2026
Same author

R<sub>3</sub>P/ICH<sub>2</sub>CH<sub>2</sub>I-Promoted Skeletal Editing of Cyclic Ethers via O/N Exchange.

Organic letters·2026
Same author

(CF<sub>3</sub>S)<sub>2</sub>C═S: Electrophilic Site at the Thiocarbonyl Sulfur for the Incorporation of Multiple CF<sub>3</sub>S Groups.

Organic letters·2025

Related Experiment Video

Updated: Jul 8, 2026

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

Ir-Catalyzed Formal 1,2-Fluorine Migration in Fluorocarbenes.

Yi-Jun Xiang1,2, Bai-Yu Qian1,2, Li-Yang Wan1

  • 1Department of Chemistry, College of Sciences, Shanghai University, 200444 Shanghai, China.

Organic Letters
|July 7, 2026
PubMed
Summary

This study introduces a new method for 1,2-fluorine migration in fluorocarbenes using an iridium catalyst. This breakthrough enables the synthesis of diverse fluorinated alkenes under mild conditions.

More Related Videos

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

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

Related Experiment Videos

Last Updated: Jul 8, 2026

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

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

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

Area of Science:

  • Organic Chemistry
  • Organometallic Chemistry
  • Fluorine Chemistry

Background:

  • 1,2-Fluorine migration in fluorocarbenes is challenging due to high kinetic barriers.
  • Developing efficient methods for synthesizing fluorinated compounds remains a key area of research.

Purpose of the Study:

  • To develop a catalytic system for formal 1,2-fluorine migration.
  • To enable straightforward access to structurally diverse fluorinated alkenes.

Main Methods:

  • Catalysis using a porphyrin-supported iridium complex.
  • Mechanistic investigations and density functional theory (DFT) calculations.

Main Results:

  • Achieved formal 1,2-fluorine migration of trifluoromethyl and pentafluoroethyl diazo compounds.
  • Elucidated a catalytic cycle involving iridium-carbene formation and intermolecular fluoride transfer.
  • Demonstrated fluoride as a chain carrier promoting fluorine migration.

Conclusions:

  • The developed catalytic platform overcomes intrinsic limitations of fluorine migration in fluorocarbenes.
  • Provides a complementary synthetic route to valuable fluorinated alkene scaffolds.