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Metal-Catalyzed Thermal Reactions of Cyclic β‑Dicarbonyl Phenyliodonium Ylide with Styrenes

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posted on 2015-01-16, 00:00 authored by Alexandra-Eleni Bosnidou, Dimitra Kalpogiannaki, Sofia Karanestora, John A. Nixas, Lazaros P. Hadjiarapoglou
A cyclic β-dicarbonyl phenyliodonium ylide reacted with various substituted styrenes under Rh2(OAc)4 catalysis to give cyclopropanes and dihydrofurans in a highly regioselective fashion. When styrenes with electron-donating substituents or disubstituted were employed, only dihydrofurans were isolated instead. A mechanism involving two competing pathways rationalizes the results.

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