Apparent electrophilic fluorination of 1,3-dicarbonyl compounds using nucleophilic fluoride mediated by PhI(OAc)2
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.
Nash, Toby J.,Pattison, Graham
supporting information
p. 3779 - 3786
(2015/06/16)
Benzamides
The present invention is directed to benzamide containing compounds which inhibit the P2X7 receptor
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Paragraph 0108
(2014/05/07)
Direct fluorination of 1,3-dicarbonyl compounds
In acid media, 1,3-diketones and 1,3-keloesters can be fluorinated in high yield and often with high conversion mainly to the corresponding 2-fluoro- compounds. Diesters such as diethyl malonate do not react with fluorine under the same reaction conditions. The mechanism of these reactions has been investigated and while the identity of the electrophilic fluorinating species is uncertain, we believe that the essential features of the reaction pathway are understood. Copyright
Chambers, Richard D.,Greenhall, Martin P.,Hutchinson, John
p. 1 - 8
(2007/10/02)
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