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À propos de : Preparation and Addition−Elimination Reactions of Benzylα,β,β-Trifluoroacrylate. A New Stereoselective Approach to(Z)-β-Substituted α,β-Difluoroacrylates        

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  • Preparation and Addition−Elimination Reactions of Benzylα,β,β-Trifluoroacrylate. A New Stereoselective Approach to(Z)-β-Substituted α,β-Difluoroacrylates
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  • Benzyl α,β,β-trifluoroacrylate (1) was prepared in good yield via the reductive Br−F elimination ofbenzyl 2-bromo-2,3,3,3-tetrafluoropropanoate or the palladium-catalyzed cross-coupling reaction of 1,2,2-trifluorovinylstannane with benzyl chloroformate. On treating 1 with various Grignard reagents ordialkylzinc reagents in the presence of copper(I) salt, the corresponding β-substituted α,β-difluoroacrylateswere obtained in high yields with high Z-selectivity. Additionally, trialkylaluminum reagents were alsofound to be good nucleophiles, the corresponding addition−elimination products being afforded in goodyields but with low stereoselectivity.
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