Expansion of substrate scope for nitroxyl radical/copper-catalyzed aerobic oxidation of primary alcohols: A guideline for catalyst selection

Yusuke Sasano, Aoto Yamaichi, Ryota Sasaki, Shota Nagasawa, Yoshiharu Iwabuchi

Research output: Contribution to journalArticlepeer-review

Abstract

Four distinctive sets of optimum nitroxyl radical/copper salt/additive catalyst combinations have been identified for accommodating the aerobic oxidation of various types of primary alcohols to their corresponding aldehydes. Interestingly, less nucleophilic catalysts exhibited higher catalytic activities for the oxidation of particular primary allylic and propargylic alcohols to give α,β-unsaturated aldehydes that function as competent Michael acceptors. The optimum conditions identified herein were successful in the oxidation of various types of primary alcohols, including unprotected amino alcohols and divalent-sulfur-containing alcohols in good-to-high yields. Moreover, N-protected alaninol, an inefficient substrate in the nitroxyl radical/ copper-catalyzed aerobic oxidation, was oxidized in good yield. On the basis of the optimization results, a guideline for catalyst selection has been established.

Original languageEnglish
Pages (from-to)488-497
Number of pages10
JournalChemical and Pharmaceutical Bulletin
Volume69
Issue number5
DOIs
Publication statusPublished - 2021 May 1

Keywords

  • Alcohol
  • Chemoselectivity
  • Copper
  • Nitroxyl radical
  • Oxidation

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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