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
Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

2.1K
Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
2.1K
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

9.9K
Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
9.9K
Sharpless Epoxidation02:57

Sharpless Epoxidation

3.8K
The conversion of allylic alcohols into epoxides using the chiral catalyst was discovered by K. Barry Sharpless and is known as Sharpless epoxidation. The use of a chiral catalyst enables the formation of one enantiomer of the product in excess. This chiral catalyst is mainly a chiral complex of titanium tetraisopropoxide and tartrate ester (specific stereoisomer). The stereoisomer used in the chiral catalyst dictates the formation of the enantiomer of the product. In other words, the use of...
3.8K
Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

3.3K
Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
3.3K
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

13.9K
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...
13.9K

You might also read

Related Articles

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

Sort by
Same author

Harnessing CO<sub>2</sub> Radical Anion-Mediated Electron Transfer for Scalable Copper-Catalyzed Cross-Coupling.

Journal of the American Chemical Society·2025
Same author

Trifluoromethylation of alkyl electrophiles with <sup>11</sup>C- or <sup>18</sup>F-labeled fluoroform for PET applications.

Science (New York, N.Y.)·2025
Same author

Enantioconvergent copper-catalysed difluoromethylation of alkyl halides.

Nature catalysis·2025
Same author

Synthesis of chiral difluoromethyl cyclopropanes through desymmetric difluoromethylation of cyclopropenes enabled by enantioselective copper catalysis.

Nature synthesis·2025
Same author

Overcoming Copper Reduction Limitation in Asymmetric Substitution: Aryl-Radical-Enabled Enantioconvergent Cyanation of Alkyl Iodides.

Journal of the American Chemical Society·2024
Same author

Catalytically Relevant Organocopper(III) Complexes Formed through Aryl-Radical-Enabled Oxidative Addition.

Journal of the American Chemical Society·2024

Related Experiment Video

Updated: Jun 10, 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

6.4K

Highly Enantioselective Decarboxylative Difluoromethylation.

Xian Zhao1, Chao Wang1, Lingfeng Yin1

  • 1Department of Chemistry, University of Cincinnati, Cincinnati, Ohio 45221, United States.

Journal of the American Chemical Society
|October 15, 2024
PubMed
Summary

Researchers developed a new nickel-catalyzed reaction to create enantioselective difluoromethylated molecules from carboxylic acids. This method efficiently installs difluoromethyl (CF2H) groups, crucial for pharmaceutical applications.

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

10.2K
Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
11:04

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine

Published on: June 13, 2022

2.9K

Related Experiment Videos

Last Updated: Jun 10, 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

6.4K
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

10.2K
Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
11:04

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine

Published on: June 13, 2022

2.9K

Area of Science:

  • Organic Chemistry
  • Fluorine Chemistry
  • Catalysis

Background:

  • Organofluorine compounds with difluoromethyl (CF2H) groups are vital in pharmaceuticals for their lipophilic hydrogen bond donating properties.
  • Enantioselective synthesis of CF2H-containing molecules is challenging but crucial for drug development.

Purpose of the Study:

  • To develop an efficient and enantioselective method for installing difluoromethyl groups into readily available starting materials.
  • To explore the utility of nickel catalysis in decarboxylative difluoromethylation.

Main Methods:

  • A novel nickel-catalyzed decarboxylative difluoromethylation reaction was developed.
  • The reaction converts alkyl carboxylic acids into difluoromethylated products.

Main Results:

  • Exceptional enantioselectivity was achieved in the difluoromethylation process.
  • The protocol demonstrated broad functional group tolerance.
  • The method is applicable to synthesizing fluorinated bioisosteres of biologically relevant molecules.

Conclusions:

  • A new, highly enantioselective nickel-catalyzed method for difluoromethylation has been established.
  • This protocol offers a valuable tool for accessing important fluorinated pharmaceutical building blocks.