Expedient access to 18F-fluoroheteroarenes via deaminative radiofluorination of aniline-derived pyridinium salts

Ford, Joseph, Ortalli, Sebastiano, Chen, Zijun, Sap, Jeroen, Tredwell, Matthew ORCID: https://orcid.org/0000-0002-4184-5611 and Gouverneur, Veronique 2024. Expedient access to 18F-fluoroheteroarenes via deaminative radiofluorination of aniline-derived pyridinium salts. Angewandte Chemie 63 (26) , e202404945. 10.1002/anie.202404945

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Abstract

Herein, we disclose that pyridinium salts derived from abundant (hetero)anilines represent a novel precursor class for nucleophilic aromatic substitution reactions with [18F]fluoride. The value of this new 18F-fluorodeamination is demonstrated with the synthesis of over 30 structurally diverse and complex heteroaryl 18F-fluorides, several derived from scaffolds that were yet to be labelled with fluorine-18. The protocol tolerates heteroarenes and functionalities commonly found in drug discovery libraries, and is amenable to scale-up and automation on a commercial radiosynthesiser.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry Medicine Wales Research Diagnostic Pet Imaging Centre (PETIC)
Publisher:	Wiley-Blackwell
ISSN:	0044-8249
Date of First Compliant Deposit:	15 May 2024
Date of Acceptance:	16 April 2024
Last Modified:	26 Jun 2024 14:20
URI:	https://orca.cardiff.ac.uk/id/eprint/168915

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