Benzylic Fluorination Induced by a Charge-Transfer Complex with a Solvent-Dependent Selectivity Switch

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Benzylic Fluorination Induced by a Charge-Transfer Complex with a Solvent-Dependent Selectivity Switch

Madani, Amiera; Anghileri, Lucia; Heydenreich, Matthias; Möller, Heiko M.; Pieber, Bartholomäus

Organic letters, 07/2022, Volume: 24, Issue: 29

Journal Article

We present a divergent strategy for the fluorination of phenylacetic acid derivatives that is induced by a charge-transfer complex between Selectfluor and 4-(dimethylamino)pyridine. A comprehensive investigation of the conditions revealed a critical role of the solvent on the reaction outcome. In the 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.

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Madani, Amiera | Anghileri, Lucia | Heydenreich, Matthias | Möller, Heiko M. | Pieber, Bartholomäus

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