Catalytic Aerobic Chemoselective α-Oxidation of Acylpyrazoles en Route to α-Hydroxy Acid Derivatives

Seiya Taninokuchi, Ryo Yazaki, Takashi Ohshima

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Catalytic aerobic chemoselective α-oxidation of acylpyrazoles is described. Acylpyrazoles, carboxylic acid oxidation state substrates, were efficiently oxidized under aerobic conditions using TEMPO as an oxygenating agent. The mild catalytic conditions of the present catalysis were amenable to late-stage α-oxidation of various pharmaceutical agents and natural products, leading to previously unreported α-hydroxy acid derivatives in short steps. Preliminary mechanistic studies revealed that in situ generated copper(II) peroxo species served as a Lewis acid/Brønsted base cooperative catalyst.

Original languageEnglish
Pages (from-to)3187-3190
Number of pages4
JournalOrganic Letters
Volume19
Issue number12
DOIs
Publication statusPublished - Jun 16 2017

Fingerprint

Lewis Acids
Hydroxy Acids
Carboxylic Acids
Biological Products
Catalysis
Copper
routes
Derivatives
Oxidation
oxidation
acids
Pharmaceutical Preparations
carboxylic acids
catalysis
catalysts
copper
Catalysts
Substrates
products
TEMPO

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Catalytic Aerobic Chemoselective α-Oxidation of Acylpyrazoles en Route to α-Hydroxy Acid Derivatives. / Taninokuchi, Seiya; Yazaki, Ryo; Ohshima, Takashi.

In: Organic Letters, Vol. 19, No. 12, 16.06.2017, p. 3187-3190.

Research output: Contribution to journalArticle

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AB - Catalytic aerobic chemoselective α-oxidation of acylpyrazoles is described. Acylpyrazoles, carboxylic acid oxidation state substrates, were efficiently oxidized under aerobic conditions using TEMPO as an oxygenating agent. The mild catalytic conditions of the present catalysis were amenable to late-stage α-oxidation of various pharmaceutical agents and natural products, leading to previously unreported α-hydroxy acid derivatives in short steps. Preliminary mechanistic studies revealed that in situ generated copper(II) peroxo species served as a Lewis acid/Brønsted base cooperative catalyst.

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