4.6 Article

Water-based efficient alkyne transformation towards α-acetoxy/imido-ketones via oxidative coupling reactions using an alkylamine catalyst

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ORGANIC & BIOMOLECULAR CHEMISTRY
卷 21, 期 25, 页码 5225-5233

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ROYAL SOC CHEMISTRY
DOI: 10.1039/d3ob00582h

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This study presents a novel approach for the expedited synthesis of valuable alpha-substituted ketones, using aliphatic amine catalysis to drive the oxidative C-O/C-N coupling reaction between alkynes and an appropriate nucleophile. The one-pot synthesis employs hypervalent iodine as both the oxidant and coupling agent. A fast, metal-free, and environmentally benign method is developed for synthesising alpha-acetoxyketones and alpha-imidoketones in an aqueous medium. To demonstrate the potential for larger-scale production, a gram-scale reaction is conducted. Moreover, this methodology has successfully enabled the direct synthesis of cathinone, a psychoactive drug. Overall, this work holds significant promise for the efficient and sustainable synthesis of alpha-substituted ketones and the potential development of novel biologically active compounds.
A novel approach is unveiled for the expedited synthesis of valuable alpha-substituted ketones, utilising aliphatic amine catalysis to drive the oxidative C-O/C-N coupling reaction between alkynes and an appropriate nucleophile. This one-pot synthesis employs hypervalent iodine as both the oxidant and coupling agent. A fast, metal-free, and environmentally benign method is developed for synthesising alpha-acetoxyketones and alpha-imidoketones in an aqueous medium. To demonstrate the potential for larger-scale production, a gram-scale reaction is conducted. Moreover, the newly developed methodology has successfully enabled the direct synthesis of cathinone, a psychoactive drug. Overall, this work holds significant promise for the efficient and sustainable synthesis of alpha-substituted ketones and the potential development of novel biologically active compounds.

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