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

Toshifumi Dohi; Tohru Kamitanaka; Eisuke Mochizuki; Motoki Ito; Yasuyuki Kita

doi:10.1248/cpb.c12-00649

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

Toshifumi Dohi, Tohru Kamitanaka, Eisuke Mochizuki, Motoki Ito, Yasuyuki Kita

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Keywords: alcohol oxidation, speedy process, recycling, hypervalent iodine reagent, nitroxyl radical

JOURNAL FREE ACCESS

2012 Volume 60 Issue 11 Pages 1442-1447

DOI https://doi.org/10.1248/cpb.c12-00649

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Abstract

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.

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