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Lookup NU author(s): Arushi Garg, Nils Gerwien, Dr Alex Charlton, Dr Matt HopkinsonORCiD
This work is licensed under a Creative Commons Attribution 4.0 International License (CC BY 4.0).
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.
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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