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

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish
Pages (from-to)1434-1444
Number of pages11
JournalJournal of Organic Chemistry
Volume88
Issue number3
DOIs
Publication statusPublished - 2023 Feb 3

ASJC Scopus subject areas

  • Organic Chemistry

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