Ring-Opening Selenation of Cyclopropanol for the Selective Synthesis of β-Hydroxy-Substituted Selenylated Ketones

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.

Ring‐Opening Functionalization/Cyclization Reactions of Cycloalkanols under Transition‐Metal‐Free Conditions

“…In 2022, an interesting example of synthesis distal difunctional ketones by virtue of ring-opening functionalization of cyclopropanols was reported by the group of Hu and Ren (Scheme 16). [35] The reaction achieved various β-hydroxy selenylated ketones in good to excellent yields using water as hydroxyl source and diselenide as selenium source. Gram-scale experiment and the derivatization experiments showcased the scalability of the scenario and practicality of the product, respectively.…”

Recent Progress in Synthetic and Biological Application of Diorganyl Diselenides

“…[268] An additional ring-opening organoselenylation of cyclopropanol approach to synthesize β-hydroxy-substituted selenylated ketones 197 has been reported using diorganyl diselenides and iodine in water (Scheme 189). [269] In this reaction, the hydroxyl group derived from water and the organoselenium moiety from diselenide can be incorporated into the αand β-positions, yielding β-hydroxy selenylated ketone. The authors determined that a radical species of iodine promotes ring-opening, and an ionic species of organoselenium promotes the functionalization of the chain.…”

Ring‐Opening Cross‐Coupling/Cyclization Reaction of Cyclopropanols with Organic Compounds

“…A catalyst-free ring-opening selenation of cyclopropanols 1 in the presence of molecular iodine as an oxidant was proposed by Hu and Ren et al in 2022 (Scheme 49). 59…”