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

研究成果: Article査読

1 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)488-497
ページ数10
ジャーナルChemical and Pharmaceutical Bulletin
69
5
DOI
出版ステータスPublished - 2021 5 1

ASJC Scopus subject areas

  • 化学 (全般)
  • 創薬

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