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

6.7K
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.
6.7K
Electrophilic Aromatic Substitution: Friedel–Crafts Alkylation of Benzene01:17

Electrophilic Aromatic Substitution: Friedel–Crafts Alkylation of Benzene

7.3K
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...
7.3K
Acid Halides to Alcohols: Grignard Reaction01:15

Acid Halides to Alcohols: Grignard Reaction

2.5K
Organomagnesium halides, commonly known as Grignard reagents, convert acid halides to tertiary alcohols. The reaction requires two equivalents of the Grignard reagent and proceeds via a ketone intermediate.
Grignard reagents are a source of carbanions and function as nucleophiles. The mechanism begins with the nucleophilic attack by the carbanion at the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs,...
2.5K
Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene01:11

Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene

7.9K
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.
7.9K
Limitations of Friedel–Crafts Reactions01:26

Limitations of Friedel–Crafts Reactions

6.0K
Several restrictions limit the use of Friedel–Crafts reactions. First, the halogen in the alkyl halide must be attached to an sp3-hybridized carbon for the Friedel–Crafts reactions to occur. Vinyl or aryl halides do not react since the carbocations formed are unstable under the reaction conditions. Second, Friedel–Crafts alkylation is susceptible to carbocation rearrangement, and the major products obtained have a rearranged carbon skeleton. In contrast, the acylium ion is...
6.0K
Sample Preparation for Analysis: Advanced Techniques01:08

Sample Preparation for Analysis: Advanced Techniques

516
Accurate analysis of complex samples often requires advanced preparation techniques to achieve reliable and reproducible results. Samples containing inorganic or organic materials can be challenging to dissolve or decompose effectively. Standard sample preparation methods include acid digestion, fusion, dry ashing, and wet digestion.
Acid digestion with strong acids is commonly used to dissolve inorganic materials that are insoluble (do not dissolve) in water. This method can be useful for...
516

You might also read

Related Articles

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

Sort by
Same author

Preparation and powder X-ray diffraction study of tecovirimat hydrate solid forms.

Acta crystallographica. Section C, Structural chemistry·2026
Same author

New approach toward the synthesis of deuterated pyrazolo[1,5-<i>a</i>]pyridines and 1,2,4-triazolo[1,5-<i>a</i>]pyridines.

Beilstein journal of organic chemistry·2017
See all related articles

Related Experiment Video

Updated: Oct 17, 2025

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
06:44

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

Published on: March 24, 2018

69.2K

Ionic Liquid-Assisted Grinding: An Electrophilic Fluorination Benchmark.

Pavel A Zaikin1, Ok Ton Dyan1,2, Innokenty R Elanov1

  • 1Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of Russian Academy of Sciences, 9 Acad. Lavrentiev Ave., 630090 Novosibirsk, Russia.

Molecules (Basel, Switzerland)
|October 13, 2021
PubMed
Summary

Ionic liquids accelerate mechanochemical fluorination reactions, enabling efficient product isolation. Fluorous anion-based ionic liquids are particularly effective catalysts for this green chemistry approach.

Keywords:
aromatic substitutionelectrophilic substitutionfluorineionic liquidsmechanochemistrysolvent-free synthesis

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

6.6K
A New Straightforward Method for Lipophilicity logP Measurement using 19F NMR Spectroscopy
09:32

A New Straightforward Method for Lipophilicity logP Measurement using 19F NMR Spectroscopy

Published on: January 30, 2019

14.6K

Related Experiment Videos

Last Updated: Oct 17, 2025

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
06:44

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

Published on: March 24, 2018

69.2K
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
A New Straightforward Method for Lipophilicity logP Measurement using 19F NMR Spectroscopy
09:32

A New Straightforward Method for Lipophilicity logP Measurement using 19F NMR Spectroscopy

Published on: January 30, 2019

14.6K

Area of Science:

  • Organic Chemistry
  • Green Chemistry
  • Mechanochemistry

Background:

  • Mechanochemical fluorination offers a solvent-free alternative for introducing fluorine into organic molecules.
  • F-TEDA-BF4 is a common reagent for electrophilic fluorination.
  • Optimizing reaction conditions is crucial for efficiency and selectivity.

Purpose of the Study:

  • To investigate the impact of liquid additives, specifically ionic liquids, on mechanochemical fluorination.
  • To compare the efficacy of various ionic liquids and molecular solvents as additives.
  • To develop an improved protocol for efficient isolation of fluorinated products.

Main Methods:

  • Mechanochemical grinding of aromatic and 1,3-dicarbonyl compounds using F-TEDA-BF4.
  • Addition of catalytic amounts of various ionic liquids and molecular solvents.
  • Analysis of reaction rates, selectivity, and product yields.
  • Isolation of products via vacuum sublimation.

Main Results:

  • Substoichiometric quantities of ionic liquids significantly increase reaction rates.
  • Ionic liquid additives facilitate high yields and selectivity in fluorination.
  • A lower viscosity of ionic liquid additives correlates with higher yields and difluorination.
  • Ionic liquids featuring fluorous anions (triflate, triflimide) demonstrate superior catalytic activity.
  • The developed protocol allows for easy and efficient product isolation.

Conclusions:

  • Ionic liquids are effective catalysts for enhancing mechanochemical fluorination.
  • The choice of ionic liquid additive critically influences reaction outcomes and process efficiency.
  • Fluorous anion-based ionic liquids represent a promising class of catalysts for sustainable fluorination.