ElectrochemicalSynthesis of γ‑Lactonesfrom the Intermolecular Oxidative Coupling between Malonates and Styrenes

We report a ferrocene-mediated electrochemical intermolecular oxidative annulation between malonates and styrenes that avoids the use of excess oxidants such as Mn(OAc)<sub>3</sub>. The reaction proceeds via presumably the generation of a malonyl radical that adds to the styrene. After further anodic oxidation, the resulting benzylic carbocation is intercepted by one of the esters to deliver the desired γ-lactones.

Publication Details

Journal
Figshare
Published
2025-03-17
DOI
https://doi.org/10.1021/acs.joc.5c00228.s001
Primary Topic
Radical Photochemical Reactions
Type
article
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ElectrochemicalSynthesis of γ‑Lactonesfrom the Intermolecular Oxidative Coupling between Malonates and Styrenes

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Radical Photochemical Reactions
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ElectrochemicalSynthesis of γ‑Lactonesfrom the Intermolecular Oxidative Coupling between Malonates and Styrenes

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Abstract

We report a ferrocene-mediated electrochemical intermolecular oxidative annulation between malonates and styrenes that avoids the use of excess oxidants such as Mn(OAc)<sub>3</sub>. The reaction proceeds via presumably the generation of a malonyl radical that adds to the styrene. After further anodic oxidation, the resulting benzylic carbocation is intercepted by one of the esters to deliver the desired γ-lactones.

Figshare
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Openalex Percentile: Top 69%
Radical Photochemical Reactions
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ElectrochemicalSynthesis of γ‑Lactonesfrom the Intermolecular Oxidative Coupling between Malonates and Styrenes · Figshare (2025) | TGRS Research Map | TGRS