Photoredox nucleophilic (radio)fluorination of alkoxyamines

Ortalli, Sebastiano, Ford, Joseph, Trabanco, Andrés A., Tredwell, Matthew ORCID: https://orcid.org/0000-0002-4184-5611 and Gouverneur, Véronique 2024. Photoredox nucleophilic (radio)fluorination of alkoxyamines. Journal of the American Chemical Society 146 (17) , pp. 11599-11604. 10.1021/jacs.4c02474

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Abstract

Herein, we report a photoredox nucleophilic (radio)­fluorination using TEMPO-derived alkoxyamines, a class of substrates accessible in a single step from a diversity of readily available carboxylic acids, halides, alkenes, alcohols, aldehydes, boron reagents, and C–H bonds. This mild and versatile one-electron pathway affords radiolabeled aliphatic fluorides that are typically inaccessible applying conventional nucleophilic substitution technologies due to insufficient reactivity and competitive elimination. Automation of this photoredox process is also demonstrated with a user-friendly and commercially available photoredox flow reactor and radiosynthetic platform, therefore expediting access to labeled aliphatic fluorides in high molar activity (A m ) for (pre)­clinical evaluation.

Item Type:	Article
Date Type:	Published Online
Status:	Published
Schools:	Chemistry Medicine Wales Research Diagnostic Pet Imaging Centre (PETIC)
Additional Information:	License information from Publisher: LICENSE 1: URL: https://creativecommons.org/licenses/by/4.0/, Start Date: 2024-04-23
Publisher:	American Chemical Society
ISSN:	0002-7863
Date of First Compliant Deposit:	3 May 2024
Date of Acceptance:	19 April 2024
Last Modified:	03 May 2024 08:45
URI:	https://orca.cardiff.ac.uk/id/eprint/168688

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