The fluorination of organic compounds is an appealing strategy to modulate the physicochemical properties of molecules without affecting their geometry. Incorporating fluorine into a molecule can affect the compounds biological activity, such as the lipophilicity and metabolic stability, due to the small size and high electronegativity of these atoms. Consequently, organofluorine compounds are widely used in medicinal chemistry and agrochemistry, hence creating a demand for new and simple fluorination strategies. I will present an efficient approach for benzylic fluorinations that proceeds via a hitherto undisclosed activation of Selectfluor with 4-dimethylaminopyridine. Our protocols enable a decarboxylative fluorination of phenyl acetic acid derivatives that selectively result in the respective benzyl fluorides, as well as a direct benzylic C-H fluorination of the same substrates to obtain the corresponding α-fluoro carboxylic acids. The selectivity is solely controlled by the solvent. The mode of activation, leading to a highly active species, has been investigated using NMR- and IR spectroscopy.

Direct and decarboxylative benzylic fluorination of phenylacetic acids via base-mediated activation of selectfluor

ACS Spring 2022

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