Search research articles

ABOUT JoVE

Overview Leadership Blog JoVE Help Center

AUTHORS

Publishing Process Editorial Board Scope & Policies Peer Review FAQ Submit

LIBRARIANS

Testimonials Subscriptions Access Resources Library Advisory Board FAQ

RESEARCH

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archive

EDUCATION

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Faculty Resource Center Faculty Site

Terms & Conditions of Use

Related Concept Videos

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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.

You might also read

Related Articles

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

Sort by

Same author

Introduction: Fluorine-Specific Interactions.

Chemical reviews·2025

Same author

Lewis Acid-Initiated Cleavage of a Large Ionophore: Molecular Deactivation by Potassium Ion Binding.

ChemMedChem·2025

Same author

The Fluorinative Skeletal Rearrangement of Lumisantonin: An Unanticipated Dual Role of Selectfluor.

The Journal of organic chemistry·2025

Same author

A highly selective C-H bond fluorination unlocks conformational reporting in a complex natural product derivative.

Chemical science·2025

Same author

Catalysis of Free C-C Bond Rotation: C-F---H-X H-Bonds Find a Catalytic Role.

Journal of the American Chemical Society·2025

Same author

FON: An Innovative Fluorinated Group via Hydroetherification-Type Reactivity.

Organic letters·2024

Search research articles

Related Experiment Video

Updated: Sep 14, 2025

Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes

Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes

Published on: July 28, 2018

Selective Fluorination of Complex Molecules: Late-Stage Functionalization.

Muyuan Wang¹, Jonah Ruskin¹, Joseph Marques¹

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

Chemical Reviews

|July 21, 2025

Summary

This summary is machine-generated.

Late-stage fluorination enables efficient conversion of existing compounds into valuable fluorinated molecules. This perspective reviews key strategies for single-atom modifications of complex molecules, including pharmaceuticals.

More Related Videos

18F-Labeling of Radiotracers Functionalized with a Silicon Fluoride Acceptor SiFA for Positron Emission Tomography

18F-Labeling of Radiotracers Functionalized with a Silicon Fluoride Acceptor SiFA for Positron Emission Tomography

Published on: January 11, 2020

High-throughput Synthesis of Carbohydrates and Functionalization of Polyanhydride Nanoparticles

High-throughput Synthesis of Carbohydrates and Functionalization of Polyanhydride Nanoparticles

Published on: July 6, 2012

Related Experiment Videos

Last Updated: Sep 14, 2025

Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes

Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes

Published on: July 28, 2018

18F-Labeling of Radiotracers Functionalized with a Silicon Fluoride Acceptor SiFA for Positron Emission Tomography

18F-Labeling of Radiotracers Functionalized with a Silicon Fluoride Acceptor SiFA for Positron Emission Tomography

Published on: January 11, 2020

High-throughput Synthesis of Carbohydrates and Functionalization of Polyanhydride Nanoparticles

High-throughput Synthesis of Carbohydrates and Functionalization of Polyanhydride Nanoparticles

Published on: July 6, 2012

Area of Science:

Organic Chemistry
Medicinal Chemistry
Fluorine Chemistry

Background:

Fluorination reactions have a rich history spanning over 160 years.
Incorporating fluorine into bioactive molecules offers significant advantages.
Late-stage fluorination emerged as an efficient strategy in the 21st century.

Purpose of the Study:

To present a comprehensive overview of late-stage fluorination strategies.
To focus on single-atom modifications of complex molecules.
To examine both nucleophilic and electrophilic fluorine sources.

Main Methods:

Review of late-stage fluorination techniques.
Analysis of methods applied to natural products, analogues, and pharmaceuticals.
Examination of nucleophilic and electrophilic fluorination reagents.

Main Results:

Development of numerous fluorination reagents and methods over decades.
Late-stage fluorination offers a more efficient route compared to de novo synthesis.
Strategies discussed are applicable to complex molecular structures.

Conclusions:

Late-stage fluorination is a well-justified and increasingly important field.
The presented strategies facilitate the efficient synthesis of fluorinated bioactive compounds.
Continued research in this area promises further advancements in drug discovery and development.