Intermolecular reductive coupling of aliphatic ketones with alkynes and alkenes by BCN photocatalysts
摘要
A photocatalytic process was developed for intermolecular reductive coupling of aliphatic ketones with alkynes/alkenes to furnish tertiary alcohols. Mechanistic studies support that boron carbonitrides (BCN) promote the single electron reduction of unactivated aliphatic ketones to generate ketyl radicals with visible light irradiation, which then react with alkynes and alkenes to afford the allylic and aliphatic alcohols, respectively. The heterogeneous photocatalytic system is compatible with diverse substrates including pharmaceutical-related molecules (43 examples) with reusability and scale-up experiments, verifying the complementary synthetic utility of this method to the homogeneous catalysts.