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Related Experiment Video

Updated: Aug 22, 2025

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

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Published on: July 28, 2018

Merging Fluorine Incorporation and Functional Group Migration.

Zhigang Ma¹, Xinxin Wu¹, Chen Zhu^1,2

¹Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou, 215123, Jiangsu, China.

Chemical Record (New York, N.Y.)

|November 11, 2022

Summary

This study introduces a versatile method for creating diverse fluorinated compounds using fluoroalkyl radical addition and functional group migration. These reactions enable efficient synthesis of complex molecules under mild conditions.

Keywords:

Alkene difunctionalization Fluoroalkylation Functional group migration Radical reaction Radical rearrangement

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

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

Area of Science:

Organic Chemistry
Fluorine Chemistry
Synthetic Methodology

Background:

Fluorinated compounds are crucial in pharmaceuticals and materials science.
Developing efficient methods for fluorine incorporation remains a key challenge.

Purpose of the Study:

To provide an overview of novel synthetic strategies for fluorinated compounds.
To highlight the utility of fluoroalkyl radical addition coupled with functional group migration (FGM).

Main Methods:

Radical fluoroalkylative difunctionalization of alkenes via intramolecular FGM.
Alkene difunctionalization using fluoroalkyl-containing bifunctional reagents via a docking-migration process.
C(sp3)-H bond fluoroalkylation via hydrogen atom transfer (HAT) and FGM.

Main Results:

Demonstrated three distinct reaction modes for fluorine incorporation.
Achieved trifluoromethylation and di-/mono-fluoroalkylation reactions.
Accomplished the migration of various functional groups including cyano, heteroaryl, and alkynyl.

Conclusions:

The combined strategy of fluoroalkyl radical addition and FGM offers a robust approach for synthesizing diverse fluorinated molecules.
These methods operate under mild conditions, enhancing their practical applicability.