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

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
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

14.1K
If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
14.1K
Halogenation of Alkenes02:46

Halogenation of Alkenes

15.5K
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.
15.5K
Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

8.5K
In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
8.5K
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

2.4K
Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
2.4K
Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

5.0K
In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
5.0K

You might also read

Related Articles

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

Sort by
Same author

Direct Regioselective para-Fluorination via I(I)/I(III) Catalysis.

Angewandte Chemie (International ed. in English)·2026
Same author

Effects of volatile anesthetics on peripheral nerve regeneration in a sciatic cut repair murine model.

Frontiers in cellular neuroscience·2026
Same author

Experimental Investigation of a Particle-Laden Droplet Impacting a Cantilever Beam.

Langmuir : the ACS journal of surfaces and colloids·2026
Same author

Mechanomyography as a novel marker of nerve dysfunction and recovery in chronic entrapment neuropathy.

Frontiers in neurology·2026
Same author

Fluorinated carbohydrate-based vaccines.

Chemical science·2026
Same author

Global epidemiological trends, distribution of NTDs and malaria, and disease burden projections for the next 15 years.

Frontiers in public health·2026

Related Experiment Video

Updated: Jun 21, 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

Regioselective fluorination of allenes enabled by I(I)/I(III) catalysis.

Zi-Xuan Wang1, Yameng Xu1, Ryan Gilmour2

  • 1Institute for Organic Chemistry, University of Münster, Corrensstraße 36, 48149, Münster, Germany.

Nature Communications
|July 9, 2024
PubMed
Summary
This summary is machine-generated.

Researchers developed a new method for synthesizing propargylic fluorides using organocatalysis and readily available allenes. This efficient process expands access to valuable fluorinated compounds for drug discovery.

More Related Videos

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
09:54

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Published on: September 12, 2018

7.7K
Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
12:27

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

Published on: September 8, 2013

10.9K

Related Experiment Videos

Last Updated: Jun 21, 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
Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
09:54

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Published on: September 12, 2018

7.7K
Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
12:27

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

Published on: September 8, 2013

10.9K

Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Fluorine Chemistry

Background:

  • Propargylic fluorides are important in medicinal chemistry due to F/H and F/OH bioisosterism.
  • Developing efficient synthesis methods for propargylic fluorides is crucial.
  • Propargylic alcohols can be converted to allenes, suggesting a pathway to propargylic fluorides.

Purpose of the Study:

  • To develop an operationally simple, organocatalysis-based strategy for synthesizing propargylic fluorides from allenes.
  • To establish a method that consolidates the bioisosteric relationship between propargylic alcohols and fluorides.
  • To explore the broader synthetic utility of this catalytic platform.

Main Methods:

  • Highly regioselective fluorination of unactivated allenes using I(I)/I(III) catalysis.
  • Utilizing an inexpensive hydrogen fluoride (HF) source as both nucleophile and Brønsted acid activator.
  • Demonstrating organocatalytic oxidation, chlorination, and arylation of allenes.

Main Results:

  • Efficient synthesis of secondary and tertiary propargylic fluorides, common in bioactive molecules.
  • Facile product derivatization and concise synthesis of multi-vicinal fluorinated products.
  • Preliminary validation of enantioselective catalysis and expansion to other functionalizations.

Conclusions:

  • The developed I(I)/I(III) catalytic strategy provides a versatile and efficient route to propargylic fluorides from allenes.
  • This method facilitates the exploration of organofluorine chemical space for molecular design.
  • The platform's potential is demonstrated through various functionalizations, accelerating drug discovery efforts.