3-Methyl-4-oxa-5-azahomoadamantane: Alkoxyamine-Type Organocatalyst for Alcohol Oxidation

摘要

The unique behavior and eminent reactivity of organic/ inorganic nitrogen oxides have continuously attracted the attention of chemists not only because of their profound chemistry, but also because of their use in various fields of material and life sciences. Herein, we report the discovery of a novel alkoxyamine-type organocatalyst, 3-methyl-4-oxa-5-azahomoadamantane (1), which enables highly efficient oxidation of primary and secondary alcohols into their corresponding carbonyl compounds using NaOCl as the terminal oxidant. The present work first shows a useful pathway from an alkoxyamine/alkoxyaminyl radical to a nitroxyl radical/oxoammonium ion under oxidative conditions (Figure 1).