One-Pot Synthesis of Fluorine-Containing Alkenes from In Situ-Generated Stabilized Phosphorus Ylides

Protonation of the highly reactive 1:1 intermediates, produced in the reaction between triphenylphosphine and dialkyl acetylenedicarboxylates, by 4-(trifluoromethyl)benzyl alcohol leads to vinyltriphenylphosphonium salts, which undergo a Michael addition reaction with a conjugate base to produce the corresponding fluorine-containing stabilized phosphorus ylides. An intermolecular Wittig reaction of the fluorine-containing stabilized phosphorus ylides with ninhydrin leads to the corresponding highly electron-poor fluorine-containing alkenes.

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