Safe and Scalable Aerobic Oxidation by 2-Azaadamantan-2-ol (AZADOL)/NO x Catalysis: Large-Scale Preparation of Shi's Catalyst

Yusuke Sasano, Hikaru Sato, Shinsuke Tadokoro, Masami Kozawa, Yoshiharu Iwabuchi

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)


A method for safe and scalable aerobic alcohol oxidation using 2-azaadamantan-2-ol (AZADOL), an azaadamantane-type hydroxylamine catalyst, with a NO x cocatalyst in a conventional batch reactor has been developed. The use of 2 mol % AZADOL and 10 mol % NaNO 2 was determined to promote aerobic alcohol oxidation quantitatively within a reasonable time (8 h). Safety is ensured by controlling the reaction temperature below the flash point of the acetic acid solvent. The robustness of the developed method is demonstrated by the 500 g scale oxidation of diacetone fructose into Shi's catalyst for asymmetric epoxidation.

Original languageEnglish
Pages (from-to)571-577
Number of pages7
JournalOrganic Process Research and Development
Issue number4
Publication statusPublished - 2019 Apr 19


  • NO
  • aerobic oxidation
  • alcohol oxidation
  • hydroxylamine
  • nitroxyl radical
  • oxoammonium

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry


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