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Journal Article

Benzylic fluorination induced by a charge-transfer complex with a solvent-dependent selectivity switch

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Madani,  Amiera
Bartholomäus Pieber, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Anghileri,  Lucia
Bartholomäus Pieber, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Pieber,  Bartholomäus       
Bartholomäus Pieber, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Citation

Madani, A., Anghileri, L., Heydenreich, M., Möller, H. M., & Pieber, B. (2022). Benzylic fluorination induced by a charge-transfer complex with a solvent-dependent selectivity switch. Organic Letters, 24(29), 5376-5380. doi:10.1021/acs.orglett.2c02050.


Cite as: https://hdl.handle.net/21.11116/0000-000A-C505-2
Abstract
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.