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

6.2K
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.
6.2K
Electron Affinity03:07

Electron Affinity

35.8K
The electron affinity (EA) is the energy change for adding an electron to a gaseous atom to form an anion (negative ion).
35.8K
ortho–para-Directing Deactivators: Halogens01:24

ortho–para-Directing Deactivators: Halogens

5.7K
Halogens are ortho–para directors. They are more electronegative than carbon. Therefore, as ring substituents, they can withdraw electrons through the inductive effect and deactivate the aromatic ring towards electrophilic substitution. Halogens also have an electron-donating resonance effect on the ring, which influences the orientation of the incoming electrophile. If an electrophile attacks at the ortho or the para position, the halogen donates electrons and stabilizes the intermediate...
5.7K
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

2.6K
Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
2.6K
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

8.4K
Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
8.4K
Electrophiles02:28

Electrophiles

10.9K
This lesson explains the definition, classification, and characteristic features of an electrophile that are key features of nucleophilic substitution reactions. An analysis of their charge and orbital picture helps understand their reactivity for seeking electrons. Electrophiles can be classified into positive and neutral species. Other classes include free radicals and polar functional groups.
While a positive electrophile, like a proton, reacts due to its vacant, low-energy 1s orbital, the...
10.9K

You might also read

Related Articles

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

Sort by
Same author

Transcranial direct current stimulation alleviates depression-like behaviors by activating the ACC-ZI neural circuit.

Brain research bulletin·2026
Same author

A ROS-Responsive DNA Nanodevice for Targeted Cytosolic siRNA Delivery in Metabolic Dysfunction-Associated Steatohepatitis.

Journal of the American Chemical Society·2026
Same author

Faecalibaculum rodentium- derived quinic acid- mediated Treg differentiation drives the attenuation intestinal inflammation by Agrimoniae Herba polysaccharides.

Carbohydrate polymers·2026
Same author

Efficacy of blood flow restriction training in chronic ankle conditions: a systematic review and meta-analysis.

BMC musculoskeletal disorders·2026
Same author

A Hybrid Machine Learning Framework to Improve Morphological Trait Recovery in Avian Datasets.

Ecology and evolution·2026
Same author

Secondary salinization in facility agricultural soils detrimentally affects the spatial distribution of earthworm communities: dominant drivers and ecological risks.

Journal of environmental management·2026

Related Experiment Video

Updated: Aug 12, 2025

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

6.5K

An Electrochemical Approach to Directed Fluorination.

Eric Holt1, Muyuan Wang1, Stefan Andrew Harry1

  • 1Department of Chemistry, Johns Hopkins University, 3400 N. Charles Street, Baltimore, Maryland 21218, United States.

The Journal of Organic Chemistry
|January 26, 2023
PubMed
Summary

This study introduces a new electrochemical C-H fluorination method for organic chemistry. The technique efficiently fluorinates various steroid-based molecules using readily available reagents and electrodes.

More Related Videos

Reductive Electropolymerization of a Vinyl-containing Poly-pyridyl Complex on Glassy Carbon and Fluorine-doped Tin Oxide Electrodes
09:17

Reductive Electropolymerization of a Vinyl-containing Poly-pyridyl Complex on Glassy Carbon and Fluorine-doped Tin Oxide Electrodes

Published on: January 30, 2015

12.0K
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

10.4K

Related Experiment Videos

Last Updated: Aug 12, 2025

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

6.5K
Reductive Electropolymerization of a Vinyl-containing Poly-pyridyl Complex on Glassy Carbon and Fluorine-doped Tin Oxide Electrodes
09:17

Reductive Electropolymerization of a Vinyl-containing Poly-pyridyl Complex on Glassy Carbon and Fluorine-doped Tin Oxide Electrodes

Published on: January 30, 2015

12.0K
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

10.4K

Area of Science:

  • Organic Chemistry
  • Electrochemistry
  • Fluorination Reactions

Background:

  • Electrosynthesis is experiencing a resurgence in organic chemistry, particularly for radical-mediated transformations.
  • C-H functionalization offers a powerful strategy for molecular modification.

Purpose of the Study:

  • To develop a simple, directed, and electrochemical method for C-H fluorination.
  • To expand the scope of substrates amenable to electrochemical fluorination.

Main Methods:

  • Utilized a dabconium mediator and commercially available Selectfluor.
  • Employed readily available Reticulated Vitreous Carbon (RVC) electrodes.
  • Applied the method to steroid-based substrates with directing groups.

Main Results:

  • Achieved regioselective C-H fluorination on a variety of steroid derivatives.
  • Demonstrated successful fluorination of enones, ketones, and hydroxyl groups.
  • Reported novel electrochemical fluorination of lactams, imides, lactones, and esters.

Conclusions:

  • The developed method provides a straightforward and efficient route for directed C-H fluorination.
  • This work expands the utility of electrosynthesis in introducing fluorine into complex organic molecules.
  • The method's applicability to diverse functional groups, including previously unreported ones, highlights its potential.