Late‐Stage 18F‐Difluoromethyl Labeling of N‐Heteroaromatics with High Molar Activity for PET Imaging

Despite a growing interest in CHF2 in medicinal chemistry, there is a lack of efficient methods for the insertion of CHF18F into druglike compounds. Herein described is a photoredox flow reaction for 18F‐difluoromethylation of N‐heteroaromatics that are widely used in medicinal chemistry. Following...

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Bibliographic Details
Published inAngewandte Chemie Vol. 131; no. 37; pp. 13283 - 13288
Main Authors Trump, Laura, Lemos, Agostinho, Lallemand, Bénédicte, Pasau, Patrick, Mercier, Joël, Lemaire, Christian, Luxen, André, Genicot, Christophe
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 09.09.2019
Subjects
Biological activity
C-H-Aktivierung
Chemical synthesis
Chemistry
Durchflusschemie
Fluor
Fluorine isotopes
In vivo methods and tests
Organic chemistry
Pharmaceutical sciences
Photochemie
Positron emission
Radiochemie
Reagents
Substrates
Tomography
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Summary:Despite a growing interest in CHF2 in medicinal chemistry, there is a lack of efficient methods for the insertion of CHF18F into druglike compounds. Herein described is a photoredox flow reaction for 18F‐difluoromethylation of N‐heteroaromatics that are widely used in medicinal chemistry. Following the two‐step synthesis for a new 18F‐difluoromethylation reagent, the photoredox reaction is completed within two minutes and proceeds by C−H activation, circumventing the need for pre‐functionalization of the substrate. The method is operationally simple and affords straightforward access to radiolabeled N‐heteroaromatics with high molar activity suitable for biological in vivo studies and clinical application. Eine neue Flow‐Photoredox‐Methode ermöglicht die 18F‐Difluormethylierung von Heteroaromaten durch C‐H‐Aktivierung. Das Verfahren ist auf eine breite Spanne von Heteroaromaten anwendbar und kann zur Herstellung von Radiotracern mit hoher molarer Aktivität verwendet werden, die für PET‐Studien geeignet sind.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201907488