2-Azaadamantane N-Oxyl (AZADO) and 1-Me-AZADO: Highly Efficient Organocatalysts for Oxidation of Alcohols
Masatoshi Shibuya, Masaki Tomizawa, Iwao Suzuki and Yoshiharu Iwabuchi*
*Department of Organic Chemistry, Graduate School of
Pharmaceutical Sciences, Tohoku University, 6-3 Aobayama, Sendai 980-8578, Japan, Email:
y-iwabuchi
m.tohoku.ac.jp
M. Shibuya, M. Tomizawa, I. Suzuki, Y. Iwabuchi, J. Am. Chem. Soc., 2006, 128, 8412-8413.
DOI: 10.1021/ja0620336
see article for more reactions
Abstract
A stable nitroxyl radical class of catalysts, 2-azaadamantane N-oxyl (AZADO) and 1-Me-AZADO, exhibit superior catalytic proficiency to TEMPO, converting various sterically hindered alcohols to the corresponding carbonyl compounds in excellent yields.
see article for more examples
Organocatalytic One-Pot Oxidative Cleavage of Terminal Diols to Dehomologated Carboxylic Acids
M. Shibuya, R. Doi, T. Shibuta, S.-i. Uesugi, Y. Iwabuchi, Org. Lett., 2012, 14, 5006-5009.
Key Words
AZADO, TEMPO, bleach, synthesis of ketones, Organocatalysis
ID: J48-Y2006-4920
