Highly efficient aerobic oxidation of alcohols by using less-hindered nitroxyl-radical/copper catalysis: Optimum catalyst combinations and their substrate scope

Yusuke Sasano, Naoki Kogure, Tomohiro Nishiyama, Shota Nagasawa, Yoshiharu Iwabuchi

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)

Abstract

The oxidation of alcohols into their corresponding carbonyl compounds is one of the most fundamental transformations in organic chemistry. In our recent report, 2-azaadamantane N-oxyl (AZADO)/copper catalysis promoted the highly chemoselective aerobic oxidation of unprotected amino alcohols into amino carbonyl compounds. Herein, we investigated the extension of the promising AZADO/copper-catalyzed aerobic oxidation of alcohols to other types of alcohol. During close optimization of the reaction conditions by using various alcohols, we found that the optimum combination of nitroxyl radical, copper salt, and solution concentration was dependent on the type of substrate. Various alcohols, including highly hindered and heteroatom-rich ones, were efficiently oxidized into their corresponding carbonyl compounds under mild conditions with lower amounts of the catalysts.

Original languageEnglish
Pages (from-to)1004-1009
Number of pages6
JournalChemistry - An Asian Journal
Volume10
Issue number4
DOIs
Publication statusPublished - 2015 Apr

Keywords

  • alcohols
  • copper
  • homogeneous catalysis
  • oxidation
  • radicals

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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