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

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.

Automated summary

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.