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Radical "Link-and-Lose" Strategies for Iterative C-F Functionalization of Polyfluoroarenes.

Parul Sharma¹, Jimmie D Weaver¹

¹Department of Chemistry, Oklahoma State University, Stillwater, Oklahoma, 74078, United States.

Chem

|June 18, 2026

Summary

Researchers developed a new pyridine-boryl radical method for selectively functionalizing strong carbon-fluorine bonds in polyfluoroarenes. This iterative strategy allows for multiple C-F bond transformations, creating valuable fluorinated compounds.

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Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Area of Science:

Organic Chemistry
Synthetic Chemistry

Background:

Carbon-fluorine (C-F) bonds are exceptionally strong and inert, posing a significant challenge for selective chemical modification.
Developing methods for targeted C-F bond activation is crucial for synthesizing novel fluorinated organic molecules.

Purpose of the Study:

To introduce a novel strategy for the iterative and selective functionalization of C-F bonds in polyfluoroarenes.
To enable the transformation of multiple C-F bonds beyond the first one, addressing a key limitation in current synthetic methodologies.

Main Methods:

Utilized a pyridine-boryl radical-mediated approach.
Developed an iterative "link-and-lose" strategy for sequential C-F bond functionalization.
Applied the method to polyfluoroarene substrates.

Main Results:

Achieved selective activation and functionalization of the second, third, and fourth C-F bonds in polyfluoroarenes.
Demonstrated the ability to iteratively modify multiple C-F bonds within the same molecule.
Generated a diverse range of complex fluorinated scaffolds.

Conclusions:

The pyridine-boryl radical-mediated "link-and-lose" strategy offers a powerful new tool for C-F bond functionalization.
This method provides access to previously difficult-to-synthesize fluorinated compounds relevant to medicinal chemistry.
The work overcomes limitations in iterative C-F bond activation, expanding synthetic possibilities.