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, Yoshiharu Iwabuchi

研究成果: ジャーナルへの寄稿学術論文査読

2 被引用数 (Scopus)

抄録

8-Azabicyclo[3.2.1]octan-8-ol (ABOOL) and 7-azabicyclo[2.2.1]heptan-7-ol (ABHOL) are the main homologues of hydroxylamine 2-azaadamantan-2-ol (AZADOL) and 9-azabicyclo[3.3.1]nonan-9-ol. Both homologues feature a small bicyclic backbone and are known to be stable; however, to date, they have not been used as catalysts for alcohol oxidation. Herein, we report that 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. Furthermore, we show that ABOOL and ABHOL can be easily synthesized from commercially available materials.

本文言語英語
ページ(範囲)1434-1444
ページ数11
ジャーナルJournal of Organic Chemistry
88
3
DOI
出版ステータス出版済み - 2023 2月 3

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