Benzylic C(sp3)-H fluorination

Alexander P Atkins; Alice C Dean; Alastair J J Lennox

doi:10.3762/bjoc.20.137

Benzylic C(sp³)-H fluorination

Beilstein J Org Chem. 2024 Jul 10:20:1527-1547. doi: 10.3762/bjoc.20.137. eCollection 2024.

Authors

Alexander P Atkins¹, Alice C Dean¹, Alastair J J Lennox¹

Affiliation

¹ University of Bristol, School of Chemistry, Bristol, BS8 1TS, U.K.

Abstract

The selective fluorination of C(sp³)-H bonds is an attractive target, particularly for pharmaceutical and agrochemical applications. Consequently, over recent years much attention has been focused on C(sp³)-H fluorination, and several methods that are selective for benzylic C-H bonds have been reported. These protocols operate via several distinct mechanistic pathways and involve a variety of fluorine sources with distinct reactivity profiles. This review aims to give context to these transformations and strategies, highlighting the different tactics to achieve fluorination of benzylic C-H bonds.

Keywords: C–H functionalization; benzylic; fluorination; photoredox catalysis.

Publication types

Review

Grants and funding

We would like to thank the Royal Society (University Research Fellowship and Enhancement Awards to AJJL), the EPSRC (EP/T51763X/1, EP/S024107/1), the European Research Council (949821, SENF) and Syngenta for generous funding.