Benzylic fluorination induced by a charge-transfer complex with a solvent-dependent selectivity switch
Madani A, Anghileri L, Heydenreich M, Möller HM, Pieber B. 2022. Benzylic fluorination induced by a charge-transfer complex with a solvent-dependent selectivity switch. Organic Letters. 24(29), 5376–5380.
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Author
Madani, Amiera;
Anghileri, Lucia;
Heydenreich, Matthias;
Möller, Heiko M.;
Pieber, BartholomäusISTA 
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.
Publishing Year
Date Published
2022-07-17
Journal Title
Organic Letters
Volume
24
Issue
29
Page
5376–5380
ISSN
eISSN
IST-REx-ID
Cite this
Madani A, Anghileri L, Heydenreich M, Möller HM, Pieber B. Benzylic fluorination induced by a charge-transfer complex with a solvent-dependent selectivity switch. Organic Letters. 2022;24(29):5376–5380. doi:10.1021/acs.orglett.2c02050
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. American Chemical Society. https://doi.org/10.1021/acs.orglett.2c02050
Madani, Amiera, Lucia Anghileri, Matthias Heydenreich, Heiko M. Möller, and Bartholomäus Pieber. “Benzylic Fluorination Induced by a Charge-Transfer Complex with a Solvent-Dependent Selectivity Switch.” Organic Letters. American Chemical Society, 2022. https://doi.org/10.1021/acs.orglett.2c02050.
A. Madani, L. Anghileri, M. Heydenreich, H. M. Möller, and B. Pieber, “Benzylic fluorination induced by a charge-transfer complex with a solvent-dependent selectivity switch,” Organic Letters, vol. 24, no. 29. American Chemical Society, pp. 5376–5380, 2022.
Madani A, Anghileri L, Heydenreich M, Möller HM, Pieber B. 2022. Benzylic fluorination induced by a charge-transfer complex with a solvent-dependent selectivity switch. Organic Letters. 24(29), 5376–5380.
Madani, Amiera, et al. “Benzylic Fluorination Induced by a Charge-Transfer Complex with a Solvent-Dependent Selectivity Switch.” Organic Letters, vol. 24, no. 29, American Chemical Society, 2022, pp. 5376–5380, doi:10.1021/acs.orglett.2c02050.
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