Synthesis 2015; 47(17): 2554-2569
DOI: 10.1055/s-0034-1378824
short review
© Georg Thieme Verlag Stuttgart · New York

Recent Advances in Radical Fluorination

Claire Chatalova-Sazepin
a   Chemistry Department, University of British Columbia, 2036 Main Mall, Vancouver, British Columbia, V6T 1Z1, Canada   Email: gsammis@chem.ubc.ca
,
Rémy Hemelaere
b   Canada 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*
b   Canada 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*
a   Chemistry Department, University of British Columbia, 2036 Main Mall, Vancouver, British Columbia, V6T 1Z1, Canada   Email: gsammis@chem.ubc.ca
› Author Affiliations
Further Information

Publication History

Received: 07 May 2015

Accepted after revision: 06 July 2015

Publication Date:
03 August 2015 (online)


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