SNAr Radiofluorination with In Situ Generated [18F]Tetramethylammonium Fluoride

SNAr Radiofluorination with In Situ Generated [18F]Tetramethylammonium Fluoride

This report describes a method for the nucleophilic radiofluorination of (hetero)­aryl chlorides, (hetero)­aryl triflates, and nitroarenes using a combination of [18F]­KF·K2.2.2 and Me4NHCO3 for the in situ formation of a strongly nucleophilic fluorinating reagent (proposed to be [18F]­Me4NF). This...

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Veröffentlicht in:Journal of organic chemistry 2021-10, Vol.86 (20), p.14121-14130
Hauptverfasser: Lee, So Jeong, Morales-Colón, María T, Brooks, Allen F, Wright, Jay S, Makaravage, Katarina J, Scott, Peter J. H, Sanford, Melanie S
Format: Artikel
Sprache:eng
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Zusammenfassung:This report describes a method for the nucleophilic radiofluorination of (hetero)­aryl chlorides, (hetero)­aryl triflates, and nitroarenes using a combination of [18F]­KF·K2.2.2 and Me4NHCO3 for the in situ formation of a strongly nucleophilic fluorinating reagent (proposed to be [18F]­Me4NF). This method is applied to 24 substrates bearing diverse functional groups, and it generates [18F]­(hetero)­aryl fluoride products in good to excellent radiochemical yields in the presence of ambient air/moisture. The reaction is applied to the preparation of 18F-labeled HQ-415 for potential (pre)­clinical use.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c01491