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Updated: Aug 26, 2025

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Ring-Opening Selenation of Cyclopropanol for the Selective Synthesis of β-Hydroxy-Substituted Selenylated Ketones
Jun Yao1, Dandan Hu1, Jun-Qi Zhang1
1Advanced Research Institute and Department of Chemistry, Taizhou University, Jiaojiang 318000, China.
Abstract:
Ring opening of cycloalkanols has been employed as a commonly used strategy to prepare diverse distal functionalized ketones. However, most of these ketones obtained by this strategy belong to monofunctional ketones, while difunctional ketones with more potential application value have been rarely reported. Herein, we first reported a mild I2-promoted ring-opening selenation of cyclopropanol to synthesize various distal difunctional ketones. In the reaction, hydroxyl (-OH) derived from water and RSe+ from diselenide can be introduced into the α- and β-positions, respectively, delivering β-hydroxy selenylated ketones in good to excellent yields.
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