Novel synthesis of F-1-alkene-1-phosphonate derivatives from F-alkanoyl chlorides and their efficient use for preparing fluoro-ga,β-enones

Trifluoroacetimidoyl halides: a potent synthetic origin

“…The protocol represents a convenient and economic route to access α,β-unsaturated trifluoromethyl ketones in contrast to Ishihara's method, which requires a four-step preparation of the imino phosphonate from pentafluoropropionic acid. 26 The synthesis of diverse N-substituted trifluoroacetimidoyl aryl ketones by 1,3-dimethylimidazolium iodide-catalyzed aroylation of trifluoroacetimidoyl chlorides with aromatic aldehydes in the presence of sodium hydride was disclosed by Yuan and co-workers as well (Scheme 10). 27 In the reaction, the aroyl anions attacked the CvN bond of the imidoyl chloride to yield trifluoroacetimidoyl ketones with the displacement of the chlorine atom.…”

Methods for the synthesis of α,β-unsaturated trifluoromethyl ketones and their use in organic synthesis

“…Perfluorocarboxylic acid chlorides can be converted via a four-stage procedure into compounds 21, which are then treated with a base (n-butyllithium, lithium diisopropylamide or sodium hydride) and with an aldehyde. 43 Ketones do not enter into this reaction.…”

α,β-Disubstituted CF3-Enones as a Trifluoromethyl Building Block: Regioselective Preparation of Totally Substituted 3-CF3-Pyrazoles

“…A great potential of these ketones was shown for the synthesis of various organofluorine compounds, including carbo- and heterocycles . Various approaches to the synthesis of α,β-unsaturated CF 3 -ketones can be found in the literature. − However, to the best of our knowledge, only a couple of works reported synthesis of α,β-diaryl-CF 3 -enones . Only four ketones of this class have been described.…”