The generation and synthetic application of stable carbanions situated in the beta position from fluorine atom(s) are described. Palladium(0)-catalyzed allylation reactions under neutral conditions proceeded smoothly in the system where a methylene group is activated by fluoroalkyl and carbonyl groups. In the above systems, the 2,2,2-trifluoroethyl moiety has been introduced onto the allylic position without the release of fluoride. Further, palladium(0)-catalyzed heterocyclization was achieved from the reaction of vinyl epoxide with 2-(trifluoromethyl)acrylate and/or 2,3,3,3-tetrafluoropropionate.
The formation and chemical behaviors of trifluoromethylated allylzinc and allenylzinc reagents
derived from the umpolung of allyl- or allenylpalladium complexes have been described. The
reactions of these reagents with aldehydes proceeded smoothly to afford highly stereocontrolled
γ-(trifluoromethyl)-δ-hydroxy α,β-unsaturated materials. Their configurations determined by the
spectral data were anti, and Z-isomers were produced from the system of allylzinc reagents.
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