title: Speedy and clean hypervalent iodine/nitroxyl radical mediated oxidation of alcohols using recyclable adamantane reagent with highly active 2-azaadamantane-N-oxyl organocatalyst.
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.
authors.affiliation: College of Pharmaceutical Sciences, Ritsumeikan University, 1–1–1 Nojihigashi, Kusatsu, Shiga 525–8577, Japan.
authors.forename: Toshifumi
authors.initials: T
authors.lastname: Dohi
authors.forename: Tohru
authors.initials: T
authors.lastname: Kamitanaka
authors.forename: Eisuke
authors.initials: E
authors.lastname: Mochizuki
authors.forename: Motoki
authors.initials: M
authors.lastname: Ito
authors.forename: Yasuyuki
authors.initials: Y
authors.lastname: Kita
mesh_terms: D000218:Adamantane / Q000031:analogs & derivatives* / Q000737:chemistry; D000438:Alcohols / Q000737:chemistry*; D002384:Catalysis; D003497:Cyclic N-Oxides / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry; D007455:Iodine / Q000737:chemistry*; D009589:Nitrogen Oxides / Q000737:chemistry*; D010084:Oxidation-Reduction
chemical_list: C522607:2-azaadamantane N-oxyl; D000438:Alcohols; D003497:Cyclic N-Oxides; D007202:Indicators and Reagents; D009589:Nitrogen Oxides; D007455:Iodine; C039900:nitroxyl; D000218:Adamantane