Identification of the Optimal Framework for Nitroxyl Radical/Hydroxylamine in Copper-Cocatalyzed Aerobic Alcohol Oxidation
Masaki Toda, Yusuke Sasano, Masaya Takahashi, Shogo Fujiki, Koki Kasabata, Tetsuya Ono, Katsuhiko Sato, Yoshitomo Kashiwagi 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. Toda, Y. Sasano, M. Takahashi, S. Fujiki, K. Kasabata, T. Ono, K. Sato, Y. Kashiwagi, Y. Iwabuchi, J. Org. Chem., 2023, 88, 1434-1444.
DOI: 10.1021/acs.joc.2c02327
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Abstract
8-Azabicyclo[3.2.1]octan-8-ol (ABOOL) and 7-azabicyclo[2.2.1]heptan-7-ol (ABHOL) feature small bicyclic backbones and are known to be stable. These hydroxylamines can efficiently catalyze the oxidation of various secondary alcohols to their corresponding ketones using molecular oxygen in ambient air as the terminal oxidant and copper cocatalysts at room temperature.
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Comparison of Catalytic Efficiencies for the Oxidation of Menthol
M. Shibuya, R. Doi, T. Shibuta, S.-i. Uesugi, Y. Iwabuchi, Org. Lett., 2012, 14, 5006-5009.
M. Hayashi, M. Shibuay, Y. Iwabuchi, J. Org. Chem., 2012, 77, 3005-3009.
Key Words
ID: J42-Y2023
