Safe and convenient nitroxyl radical and imide dual catalyzed NaOCl oxidation of alcohols to aldehydes/ketones

Naohiro Fukuda, Minoru Izumi, Tomomi Ikemoto

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

A novel and practical oxidation of alcohols to carbonyl compounds using NaOCl in the presence of catalytic amounts of imide compound and nitroxyl radical has been developed. A wide variety of aliphatic, benzylic primary alcohols, and secondary alcohols were oxidized to afford the corresponding aldehydes and ketones in up to 98% yield without undesired halogenation on aromatic rings or double bonds. The oxidation safely proceeded not only in the presence of K2CO3 but also by a slow addition of NaOCl without tedious pH adjustment.

Original languageEnglish
Pages (from-to)3905-3908
Number of pages4
JournalTetrahedron Letters
Volume56
Issue number25
DOIs
Publication statusPublished - Mar 19 2015

Fingerprint

Imides
Ketones
Aldehydes
Alcohols
Oxidation
Halogenation
Carbonyl compounds
nitroxyl

Keywords

  • Alcohol
  • Imide
  • NaOCl
  • Nitroxyl radical
  • Oxidation

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Safe and convenient nitroxyl radical and imide dual catalyzed NaOCl oxidation of alcohols to aldehydes/ketones. / Fukuda, Naohiro; Izumi, Minoru; Ikemoto, Tomomi.

In: Tetrahedron Letters, Vol. 56, No. 25, 19.03.2015, p. 3905-3908.

Research output: Contribution to journalArticle

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AB - A novel and practical oxidation of alcohols to carbonyl compounds using NaOCl in the presence of catalytic amounts of imide compound and nitroxyl radical has been developed. A wide variety of aliphatic, benzylic primary alcohols, and secondary alcohols were oxidized to afford the corresponding aldehydes and ketones in up to 98% yield without undesired halogenation on aromatic rings or double bonds. The oxidation safely proceeded not only in the presence of K2CO3 but also by a slow addition of NaOCl without tedious pH adjustment.

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