18F-Difluoromethyl(ene) motifs via oxidative fluorodecarboxylation with [18F]Fluoride

Ortalli, Sebastiano, Ford, Joseph, Szpera, Robert, Stoessel, Barbara, Trabanco, Andrés A., Tredwell, Matthew ORCID: https://orcid.org/0000-0002-4184-5611 and Gouverneur, Véronique 2024. 18F-Difluoromethyl(ene) motifs via oxidative fluorodecarboxylation with [18F]Fluoride. Organic Letters 26 (43) , pp. 9368-9372. 10.1021/acs.orglett.4c03611

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Abstract

Herein, we report that α-fluorocarboxylic acids undergo manganese-mediated oxidative 18F-fluorodecarboxylation with [18F]fluoride affording biologically relevant 18F-difluoromethyl(ene)-containing molecules. This no-carrier added process provides a solution to a known challenge in radiochemistry and expands the radiochemical space available for positron emission tomography (PET) ligand discovery. Scalability on a fully automated radiosynthetic platform is exemplified with the production of [18F]4,4-difluoropiperidine that, we demonstrate, is amenable to postlabeling functionalization including N-heteroarylation and amide as well as sulfonamide bond formation.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry Wales Research Diagnostic Pet Imaging Centre (PETIC)
Publisher:	American Chemical Society
ISSN:	1523-7060
Date of First Compliant Deposit:	31 October 2024
Date of Acceptance:	17 October 2024
Last Modified:	10 Dec 2024 13:36
URI:	https://orca.cardiff.ac.uk/id/eprint/173282

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