Apparent electrophilic fluorination of 1,3-dicarbonyl compounds using nucleophilic fluoride mediated by PhI(OAc)2

Toby J. Nash, Graham Pattison

Research output: Contribution to journalArticle

Abstract

The apparent electrophilic fluorination of 1,3-dicarbonyl compounds using Et3N·3HF as a nucleophilic fluoride source is reported. This reaction requires PhI(OAc)2 as oxidant and can be conducted safely in standard laboratory glassware. Alternative selectivity compared to Selectfluor was observed in some cases. This approach may reduce our reliance on difficult-to-handle fluorine gas and expensive electrophilic fluorinating agents derived from elemental fluorine. Mechanistic analysis related to the active fluorinating species and fluoride/acetate exchange is presented. The apparent electrophilic fluorination of 1,3-dicarbonyl compounds using Et3N·3HF mediated by the in-situ formation of PhIF2 from PhI(OAc)2 is reported. This can be performed safely in standard laboratory glassware, and this approach may reduce our reliance on difficult-to-handle fluorine gas and expensive electrophilic fluorinating agents derived from elemental fluorine.

Original languageEnglish
Pages (from-to)3779-3786
Number of pages8
JournalEuropean Journal of Organic Chemistry
Volume2015
Issue number17
DOIs
Publication statusPublished - 1 Jun 2015

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Fluorination
fluorination
Fluorine
Fluorides
fluorine
fluorides
glassware
Gases
gases
Oxidants
acetates
Ion exchange
Acetates
selectivity

Keywords

  • Fluorination
  • Hypervalent compounds
  • Iodine
  • Ligand exchange
  • Sustainable chemistry

Cite this

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abstract = "The apparent electrophilic fluorination of 1,3-dicarbonyl compounds using Et3N·3HF as a nucleophilic fluoride source is reported. This reaction requires PhI(OAc)2 as oxidant and can be conducted safely in standard laboratory glassware. Alternative selectivity compared to Selectfluor was observed in some cases. This approach may reduce our reliance on difficult-to-handle fluorine gas and expensive electrophilic fluorinating agents derived from elemental fluorine. Mechanistic analysis related to the active fluorinating species and fluoride/acetate exchange is presented. The apparent electrophilic fluorination of 1,3-dicarbonyl compounds using Et3N·3HF mediated by the in-situ formation of PhIF2 from PhI(OAc)2 is reported. This can be performed safely in standard laboratory glassware, and this approach may reduce our reliance on difficult-to-handle fluorine gas and expensive electrophilic fluorinating agents derived from elemental fluorine.",
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Apparent electrophilic fluorination of 1,3-dicarbonyl compounds using nucleophilic fluoride mediated by PhI(OAc)2. / Nash, Toby J.; Pattison, Graham.

In: European Journal of Organic Chemistry, Vol. 2015, No. 17, 01.06.2015, p. 3779-3786.

Research output: Contribution to journalArticle

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AU - Pattison, Graham

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