Copper(I)-Catalyzed Oxidation of Alkenes Using Molecular Oxygen and Hydroxylamines: Synthesis and Reactivity of α‑Oxygenated Ketones

The copper­(I)-catalyzed oxidation of alkenes with molecular oxygen and N-hydroxy­phthalimide (NHPI) or N-hydroxybenzotriazole (HOBt) provided α-oxygenated ketones. The reaction proceeded under a balloon of O₂ at room temperature to furnish the dioxygenated products in 50–90% yield. These compounds, particularly the HOBt derivatives, can be further functionalized with phosphorus, nitrogen, and sulfur nucleophiles to give synthetically useful products.