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

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.

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 Creators:
Madani, Amiera1, Author           
Anghileri, Lucia1, Author           
Heydenreich, Matthias, Author
Möller, Heiko M., Author
Pieber, Bartholomäus1, Author           
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1Bartholomäus Pieber, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_2522692              

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Free keywords: Radical fluorination; N-F bond activation; charge transfer; decarboxylative fluorination; hydrogen atom transfer
 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.

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Language(s): eng - English
 Dates: 2022-07-172022
 Publication Status: Published in print
 Pages: -
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 Table of Contents: -
 Rev. Type: -
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Title: Organic Letters
  Abbreviation : Org. Lett.
Source Genre: Journal
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Publ. Info: Washington, DC : American Chemical Society
Pages: - Volume / Issue: 24 (29) Sequence Number: - Start / End Page: 5376 - 5380 Identifier: ISSN: 1523-7060

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Title: ChemRxiv : the Preprint Server for Chemistry
  Other : ChemRxiv
Source Genre: Journal
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Publ. Info: Washington, DC; Frankfurt am Main; Cambridge, London : ACS, GDCh, Royal Society of Chemistry
Pages: - Volume / Issue: - Sequence Number: - Start / End Page: - Identifier: ZDB: 2949894-7