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By utilizing a specific solvent and highly active 2-azaadamantane-N-oxyl (AZADO) as an organocatalyst, we have improved the recycling protocol of the adamatane reagent 1 to be faster and more operationally simple for the hypervalent iodine/nitroxyl radical mediated alcohol oxidation. This very mild system can efficiently mediate the oxidation of a range of alcohols to carbonyl compounds with a broad substrate scope, and after the reactions, the reduced adamantane tetraiodide 1', which automatically precipitated from the reaction mixtures as the reactions progresses, could be directly recovered by filtration.

chemical and pharmaceutical bulletin/chemical and pharmaceutical bulletin

Speedy and Clean Hypervalent Iodine/Nitroxyl Radical Mediated Oxidation of Alcohols Using Recyclable Adamantane Reagent with Highly Active 2-Azaadamantane-&lt;i&gt;N&lt;/i&gt;-oxyl Organocatalyst