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Formal Insertion of Alkenes Into C(sp³)−F Bonds Mediated by Fluorine-Hydrogen Bonding

Lookup NU author(s): Arushi Garg, Nils Gerwien, Dr Alex Charlton, Dr Matt HopkinsonORCiD

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This work is licensed under a Creative Commons Attribution 4.0 International License (CC BY 4.0).

Abstract

C−F Insertion reactions represent an attractive approach to prepare valuable fluorinated compounds. The high strength of C−F bonds and the low reactivity of the fluoride released upon C−F bond cleavage, however, mean that examples of such processes are extremely scarce in the literature. Here we report a reaction system that overcomes these challenges using hydrogen bond donors that both activate C−F bonds and allow for downstream reactions with fluoride. In the presence of hexafluoroisopropanol, benzyl and propargyl fluorides undergo efficient formal C−F bond insertion across α-fluorinated styrenes. This process, which does not require any additional fluorinating reagent, occurs under mild conditions and delivers products featuring the gem-difluoro motif, which is attracting increasing interest in medicinal chemistry. Moreover, readily available organic bromides can be engaged directly in a one-pot process that avoids the isolation of organic fluorides.

Publication metadata

Author(s): Garg A, Gerwien NJ, Fasting C, Charlton A, Hopkinson MN

Publication type: Article

Publication status: Published

Journal: Angewandte Chemie International Edition

Year: 2023

Volume: 62

Issue: 25

Print publication date: 19/06/2023

Online publication date: 24/04/2023

Acceptance date: 20/04/2023

Date deposited: 05/05/2023

ISSN (print): 1433-7851

ISSN (electronic): 1521-3773

Publisher: Wiley-Blackwell Publishing Ltd.

URL: https://doi.org/10.1002/anie.202302860

DOI: 10.1002/anie.202302860

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