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

6.6K
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.
6.6K
Nucleophiles02:30

Nucleophiles

14.4K
The word “nucleophile” has a Greek root and translates to nucleus-loving. Nucleophiles are either negatively charged or neutral species with a pair of electrons in a high-energy occupied molecular orbital (HOMO). As these species tend to donate electron pairs, nucleophiles are considered Lewis bases as well. Negatively charged species, like OH−, Cl−, or HS−, with one or several pairs of electrons, are typically nucleophiles. Similarly, neutral species such as...
14.4K
Alkyl Halides02:45

Alkyl Halides

17.7K
Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
17.7K
Electrophiles02:28

Electrophiles

11.3K
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...
11.3K
Base-Promoted α-Halogenation of Aldehydes and Ketones00:51

Base-Promoted α-Halogenation of Aldehydes and Ketones

3.7K
α-Halogenation of aldehydes and ketones is a reaction involving the substitution of α hydrogens with halogens in the presence of a base.  The reaction begins with the abstraction of  α hydrogen by the base to produce a nucleophilic enolate ion. This intermediate undergoes a subsequent nucleophilic substitution with the halogen to produce a monohalogenated carbonyl compound. If the starting substrate has more than one α hydrogen, it is difficult to stop the reaction...
3.7K
Electron Affinity03:07

Electron Affinity

39.0K
The electron affinity (EA) is the energy change for adding an electron to a gaseous atom to form an anion (negative ion).
39.0K

You might also read

Related Articles

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

Sort by
Same author

Au(I)/Au(III)-Catalyzed Annulative Addition of Alkynes to Aryl Iodides.

Organic letters·2026
Same author

Gold-catalyzed azidation, cyanation, and alkynylation of aryl iodides from readily available TMS-N<sub>3</sub>, TMS-CN, and alkynyl-TMS.

Chemical communications (Cambridge, England)·2025
Same author

An effective and sustainable strategy to improve the stability and adhesion of thermoplastic starch to polyester/cotton yarns via the mixture of gellan gum.

International journal of biological macromolecules·2025
Same author

Synthesis of Trifluoromethylated Alkenes via a Tandem Aldol/<i>N</i>-Acyloxyphthalimide-Assisted Decarboxylation Sequence.

Organic letters·2025
Same author

Electrosynthesis of Fluoroalkenes from Alpha-CF<sub>3</sub> and Alpha-CF<sub>2</sub>H Benzyl Halides.

Chemistry (Weinheim an der Bergstrasse, Germany)·2025
Same author

Synthesis of Aryl Thiocyanates, Aryl Dithiocarbamates, Aryl Sulfones, and Aryl Thiobenzoates via Au-Catalyzed C-S Cross-Couplings.

Organic letters·2024

Related Experiment Video

Updated: Oct 11, 2025

Microwave-assisted One-pot Synthesis of N-succinimidyl-4-[18F]fluorobenzoate [18F]SFB
08:33

Microwave-assisted One-pot Synthesis of N-succinimidyl-4-[18F]fluorobenzoate [18F]SFB

Published on: June 28, 2011

13.1K

Unbalanced-Ion-Pair-Catalyzed Nucleophilic Fluorination Using Potassium Fluoride.

Wangbing Li1, Zhichao Lu2, Gerald B Hammond2

  • 1Key Laboratory of Science and Technology of Eco-Textiles, Ministry of Education, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai, 201620, China.

Organic Letters
|December 1, 2021
PubMed
Summary

A novel unbalanced ion pair promoter accelerates nucleophilic fluorination reactions using potassium fluoride. This reusable polymer-supported promoter is effective even in the presence of water and in continuous flow systems.

More Related Videos

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
09:58

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

Published on: February 24, 2015

11.4K
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

6.6K

Related Experiment Videos

Last Updated: Oct 11, 2025

Microwave-assisted One-pot Synthesis of N-succinimidyl-4-[18F]fluorobenzoate [18F]SFB
08:33

Microwave-assisted One-pot Synthesis of N-succinimidyl-4-[18F]fluorobenzoate [18F]SFB

Published on: June 28, 2011

13.1K
Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
09:58

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

Published on: February 24, 2015

11.4K
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

6.6K

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Materials Science

Background:

  • Nucleophilic fluorination is a critical transformation in synthesizing fluorinated organic compounds.
  • Traditional methods often require harsh conditions or expensive reagents.
  • Developing efficient and user-friendly fluorination protocols remains an active research area.

Purpose of the Study:

  • To develop a novel unbalanced ion pair promoter for accelerating nucleophilic fluorination reactions.
  • To create a reusable and easily handled promoter system.
  • To demonstrate the applicability of the promoter in continuous flow conditions and its tolerance to water.

Main Methods:

  • Synthesis of an unbalanced ion pair promoter using tetrabutylammonium sulfate.
  • Immobilization of the ion pair promoter onto an ion-exchange resin (A26-SO42-).
  • Evaluation of the promoter's efficiency in nucleophilic fluorination reactions with potassium fluoride (KF).
  • Testing the reusability of the polymer-supported promoter and its performance in continuous flow systems.
  • Assessing the tolerance of the reaction conditions to water.

Main Results:

  • The unbalanced ion pair promoter significantly accelerated nucleophilic fluorinations with KF.
  • The polymer-supported promoter (A26-SO42-) was successfully prepared from an inexpensive ion-exchange resin.
  • The A26-SO42- promoter demonstrated excellent reusability after simple filtration.
  • Continuous flow reactions using A26-SO42- were successful.
  • The developed method showed tolerance to water, simplifying reaction setup.

Conclusions:

  • An unbalanced ion pair promoter system offers a highly effective approach for nucleophilic fluorination.
  • The polymer-supported and reusable nature of A26-SO42- makes it a practical and sustainable reagent.
  • The promoter's utility in continuous flow and its water tolerance expand its applicability in organic synthesis.