September 23, 2025Organic Letters

Electrochemical β-Scission-Mediated Ring Contraction/Functionalization of 2-Alkylidenecyclobutanol Derivatives

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The protocol enables the synthesis of β-functionalized cyclopropanecarbaldehydes and cyclopropylketones efficiently.
Mechanistic investigations reveal the formation of a 2-alkylidenecyclobutyl oxy radical intermediate during the reaction.
The method accommodates a broad range of 2-alkylidenecyclobutanols and weak nucleophiles for functionalization.
This strategy offers an oxidant-free pathway, providing diverse access to alkoxylated, hydroxylated, fluorinated, and azidated products.

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Electrochemical approach generates diverse β-functionalized cyclopropanecarbaldehydes and cyclopropylketones, indicating a novel synthetic pathway.

Wang et al. (2025) studied this question.

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Electrochemical approach generates diverse β-functionalized cyclopropanecarbaldehydes and cyclopropylketones, indicating a novel synthetic pathway.