Expedient Access to 18 F-Fluoroheteroarenes via Deaminative Radiofluorination of Aniline-Derived Pyridinium Salts.

Autor: Ford J; Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, United Kingdom., Ortalli S; Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, United Kingdom., Chen Z; Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, United Kingdom., Sap JBI; Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, United Kingdom.; Current address: Department of Translational Imaging, Genentech Inc., 1 DNA Way, South San Francisco, CA, 94080, USA., Tredwell M; Wales Research and Diagnostic PET Imaging Centre, Cardiff University, University Hospital of Wales, Heath Park, Cardiff, CF14 4XN, United Kingdom.; School of Chemistry, Cardiff University Main Building, Park Place, Cardiff, CF10 3AT, United Kingdom., Gouverneur V; Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, United Kingdom.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2024 Jun 21; Vol. 63 (26), pp. e202404945. Date of Electronic Publication: 2024 May 24.
DOI: 10.1002/anie.202404945
Abstrakt: Herein, we disclose that pyridinium salts derived from abundant (hetero)anilines represent a novel precursor class for nucleophilic aromatic substitution reactions with [ 18 F]fluoride. The value of this new 18 F-fluorodeamination is demonstrated with the synthesis of over 30 structurally diverse and complex heteroaryl 18 F-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.
(© 2024 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.)
Databáze: MEDLINE
Externí odkaz: