¹⁹F- and ¹⁸F-Arene Deoxyfluorination via Organic Photoredox-Catalysed Polarity-Reversed Nucleophilic Aromatic Substitution.

ABSTRACT: Nucleophilic aromatic substitution (S_NAr) is routinely used to install ¹⁹F^- and ¹⁸F^- in aromatic molecules, but is typically limited to electron-deficient arenes due to kinetic barriers associated with C-F bond formation. Here we demonstrate that a polarity-reversed photoredox-catalysed arene deoxyfluorination operating via cation radical-accelerated nucleophilic aromatic substitution (CRA-S_NAr) enables the fluorination of electron-rich arenes with ¹⁹F^- and ¹⁸F^- under mild conditions, thus complementing the traditional arene polarity requirements necessary for S_NAr-based fluorination. The utility of our radiofluorination strategy is highlighted by short reaction times, c

SUBMITTER: Tay NES 

PROVIDER: S-EPMC8009013 | biostudies-literature | 2020 Sep

REPOSITORIES: biostudies-literature