Related Experiment Video
Updated: May 21, 2026
![[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)
[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
Published on: May 21, 2019
Copper-mediated fluorination of aryl iodides
Patrick S Fier1, John F Hartwig
1Department of Chemistry, University of California, Berkeley, California 94720, USA.
This study introduces a new method for synthesizing aryl fluorides, crucial compounds in pharmaceuticals and agrochemicals. The reaction efficiently converts aryl iodides into valuable aryl fluorides using copper and silver fluoride reagents.
Area of Science:
- Organic Chemistry
- Fluorine Chemistry
Background:
- Aryl fluorides are vital building blocks in pharmaceuticals, agrochemicals, and materials science.
- Their unique properties stem from the distinct electronic and steric influences of fluorine.
- Current synthetic methodologies for aryl fluorides are limited, necessitating novel approaches.
Purpose of the Study:
- To develop an efficient and versatile method for synthesizing aryl fluorides.
- To explore the conversion of readily available aryl iodides to aryl fluorides.
Main Methods:
- The study employs a cationic copper reagent in conjunction with silver fluoride.
- A diverse range of aryl iodides were subjected to the reaction conditions.
Main Results:
- Successful conversion of various aryl iodides to their corresponding aryl fluorides was achieved.
- Preliminary mechanistic investigations suggest the involvement of a cationic arylcopper(III) fluoride intermediate.
Conclusions:
- A novel synthetic route to aryl fluorides from aryl iodides has been established.
- The reaction proceeds via a facile reductive elimination pathway.
- This method offers a valuable addition to the synthetic chemist's toolkit for accessing fluorinated compounds.
More Related Videos
09:54Chemoselective 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
08:56Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
Related Concept Videos
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
Nucleophilic Aromatic Substitution: Elimination–Addition
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene
Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene