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Apparent Electrophilic Fluorination of 1,3‐Dicarbonyl Compounds Using Nucleophilic Fluoride Mediated by PhI(OAc)2

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.

Authors:   Toby J. Nash, Graham Pattison
Journal:   European Journal of Organic Chemistry
Year:   2015
Pages:   n/a
DOI:   10.1002/ejoc.201500370
Publication date:   05-May-2015
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