Highly chemoselective aerobic oxidation of amino alcohols into amino carbonyl compounds

Yusuke Sasano, Shota Nagasawa, Mai Yamazaki, Masatoshi Shibuya, Jaiwook Park, Yoshiharu Iwabuchi

Research output: Contribution to journalArticlepeer-review

105 Citations (Scopus)

Abstract

The direct oxidation of unprotected amino alcohols to their corresponding amino carbonyl compounds has often posed serious challenges in organic synthesis and has constrained chemists to adopting an indirect route, such as a protection/deprotection strategy, to attain their goal. Described herein is a highly chemoselective aerobic oxidation of unprotected amino alcohols to their amino carbonyl compounds in which 2-azaadamantane N-oxyl (AZADO)/copper catalysis is used. The catalytic system developed leads to the alcohol-selective oxidation of various unprotected amino alcohols, carrying a primary, secondary, or tertiary amino group, in good to high yield at ambient temperature with exposure to air, thus offering flexibility in the synthesis of nitrogen-containing compounds. Strong as an ox: The highly chemoselective aerobic oxidation of unprotected amino alcohols to their corresponding amino carbonyl compounds has been achieved by using 2-azaadamantane N-oxyl (AZADO)/copper catalysis. This catalytic system oxidizes not only alcohols with tertiary amino groups but also those with secondary and primary amines in good to high yield at ambient temperature in air. bpy=2,2-bipyridyl, DMAP=4-(N,N-dimethylamino)pyridine.

Original languageEnglish
Pages (from-to)3236-3240
Number of pages5
JournalAngewandte Chemie - International Edition
Volume53
Issue number12
DOIs
Publication statusPublished - 2014 Mar 17

Keywords

  • amino alcohol
  • chemoselectivity
  • copper
  • oxidation
  • radical chemistry

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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