Organic Chemistry

Benzylic fluorination induced by N–F bond activation of Selectfluor® with a solvent-dependent selectivity switch



We present a divergent radical strategy for the fluorination of phenylacetic acid derivatives through N–F bond activation of Selectfluor® with 4-(dimethylamino)pyridine. Comprehensive reaction investigation revealed the critical role of reaction media on selectivity. In presence of water, decarboxylative fluorination through a single electron oxidation is dominant. Non-aqueous conditions result in the clean formation of α-fluoro-α-arylcarboxylic acids through hydrogen atom transfer.


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Supplementary material

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Supporting Info
Experimental procedures and characterization of compounds