Practical preparation methods for highly active azaadamantane-nitroxyl- radical-type oxidation catalysts

Masatoshi Shibuya, Yusuke Sasano, Masaki Tomizawa, Toshimasa Hamada, Masami Kozawa, Noriaki Nagahama, Yoshiharu Iwabuchi

Research output: Contribution to journalArticle

58 Citations (Scopus)

Abstract

We have recently disclosed that a less hindered class of nitroxyl radicals, i.e., 2-azaadamantan-N-oxyl (AZADO), 1-Me-AZADO, and 9-azabicyclo[3.3.1]nonan- N-oxyl (ABNO), exhibit marked catalytic activity for the oxidation of alcohols with the aid of environmentally friendly oxidants, offering a green and sustainable option for current alcohol oxidation. Encouraged by their outstanding catalytic performance, we envisioned the development of scalable routes to these radicals that could be extended to the commercialization of these radicals for benchtop use as well as for industrial use as optional reagents that complement TEMPO, the flagship compound of stable nitroxyl radicals. We herein describe short and reproducible preparation methods for AZADO and 1-Me-AZADO, featuring an efficient construction of the 2-azaadamantane skeleton. 1 Introduction 2 1-Me-AZADO and AZADO: First-Generation Syntheses 3 Second-Generation Synthesis of 1-Me-AZADO 4 Synthetic Venture towards 2-Azaadamantane: Second-Generation Synthesis of AZADO 5 Conclusion.

Original languageEnglish
Article numberF76611SS
Pages (from-to)3418-3425
Number of pages8
JournalSynthesis
Issue number21
DOIs
Publication statusPublished - 2011 Oct 7

Keywords

  • adamantane
  • alcohol oxidation
  • hydroamination
  • nitroxyl radical
  • organocatalyst

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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