Recent Advances in Radical Fluorination

Claire Chatalova-Sazepin; Rémy Hemelaere; Jean-François Paquin; Glenn M. Sammis

doi:10.1055/s-0034-1378824

Synthesis, Table of Contents

Synthesis 2015; 47(17): 2554-2569
DOI: 10.1055/s-0034-1378824

short review

Recent Advances in Radical Fluorination

Authors

Claire Chatalova-Sazepin

^aChemistry Department, University of British Columbia, 2036 Main Mall, Vancouver, British Columbia, V6T 1Z1, Canada Email: gsammis@chem.ubc.ca
Rémy Hemelaere

^bCanada Research Chair in Organic and Medicinal Chemistry, Département de chimie, 1045 avenue de la Médecine, Pavillon Alexandre-Vachon, Université Laval, Québec, Québec, G1V 0A6, Canada Email: jean-francois.paquin@chm.ulaval.ca
Jean-François Paquin*

^bCanada Research Chair in Organic and Medicinal Chemistry, Département de chimie, 1045 avenue de la Médecine, Pavillon Alexandre-Vachon, Université Laval, Québec, Québec, G1V 0A6, Canada Email: jean-francois.paquin@chm.ulaval.ca
Glenn M. Sammis*

^aChemistry Department, University of British Columbia, 2036 Main Mall, Vancouver, British Columbia, V6T 1Z1, Canada Email: gsammis@chem.ubc.ca

Abstract

All articles of this category

Abstract

The importance of fluorinated compounds in pharmaceutical, agrochemical, and material chemistry has led to the development of numerous methods for electrophilic and nucleophilic fluorination. Radical fluorination represents an interesting complementary approach, but it had been limited due to the paucity of selective radical fluorinating agents. The recent uncovering of easier to handle atomic fluorine sources has led to significant advances in radical fluorination in the past few years. This review presents the newly developed methods for fluorination involving radicals as reactive intermediates.

1 Introduction

2 Atomic Fluorine Sources

2.1 Fluorine as a Selective Radical Fluorinating Agent

2.2 Fluoroxy Reagents

2.3 XeF₂

2.4 N–F Reagents as Atomic Fluorine Sources

3 Methodologies for Radical Fluorination

3.1 Decarboxylative Fluorination

3.2 Fluorination of Alkenes

3.3 Fluorination of Boronic Acid Derivatives

3.4 C(sp³)–H Fluorination

3.5 C–C Bond Activation

4 Conclusion

Key words

fluorination - radical chemistry - synthetic methods - C–H activation

Full Text

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