Stable TEMPO and ABNO Catalyst Solutions for User-Friendly (bpy)Cu/Nitroxyl-Catalyzed Aerobic Alcohol Oxidation

Two solutions, one consisting of bpy/TEMPO/NMI and the other bpy/ABNO/NMI (bpy =2,2′-bipyridyl; TEMPO = 2,2,6,6-tetramethyl­piperidine N-oxyl, ABNO = 9-azabicyclo[3.3.1]­nonane N-oxyl; NMI = N-methylimidazole), in acetonitrile are shown to have good long-term stability (≥1 year) under air at 5 °C. T...

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Bibliographic Details
Published in:Journal of organic chemistry 2015-11, Vol.80 (21), p.11184-11188
Main Authors: Steves, Janelle E, Stahl, Shannon S
Format: Article
Language:English
Subjects:
2,2'-Dipyridyl - chemistry
Alcohols - chemistry
Catalysis
Copper - chemistry
Cyclic N-Oxides - chemistry
Ligands
Molecular Structure
Nitrogen Oxides - chemistry
Organometallic Compounds - chemistry
Oxidation-Reduction
Solutions
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Summary:Two solutions, one consisting of bpy/TEMPO/NMI and the other bpy/ABNO/NMI (bpy =2,2′-bipyridyl; TEMPO = 2,2,6,6-tetramethyl­piperidine N-oxyl, ABNO = 9-azabicyclo[3.3.1]­nonane N-oxyl; NMI = N-methylimidazole), in acetonitrile are shown to have good long-term stability (≥1 year) under air at 5 °C. The solutions may be combined in appropriate quantities with commercially available [Cu­(MeCN)4]­OTf to provide a convenient catalyst system for the aerobic oxidation of primary and secondary alcohols.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b01950