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Alcohol Oxidation Catalyst Showing Higher Activity than TEMPO
Recently, environmentally friendly oxidation catalyzed by TEMPO, a nitroxy radical, has been attracting attention. Iwabuchi et al. have reported highly efficient oxidation of alcohols catalyzed by 2-azaadamantan-N-oxyl (AZADO), a nitroxy radical.1,2,3) AZADO exhibits a higher oxidation ability than TEMPO, which allows it to oxidize even hindered secondary alcohols in high yields. 2-Hydroxy-2-azaadamantane (AZADOL®"), developed by Iwabuchi et al., is a more storage-stable catalyst than AZADO. AZADOL®";" shows the same performance because of having a catalytic reaction mechanism via AZADO in the presence of oxidants. Other oxidation by oxoammonium salts derived from AZADOL®";" has been also investigated.4)
References
- 1)Y. Iwabuchi, Chem. Pharm. Bull. 2013, 61, 1197.
- 2)M. Shibuya, Y. Sasano, M. Tomizawa, T. Hamada, M. Kozawa, N. Nagahama, Y. Iwabuchi, Synthesis 2011, 3418.
- 3)Y. Iwabuchi, M. Shibuya, M. Tomizawa, Y. Osada, PCT Int. Appl. WO 2009145323, 2009.
- 4)M. Hayashi, M. Shibuya, Y. Iwabuchi, Org. Lett. 2012, 14, 154.