Mechanistic insight into catalytic aerobic chemoselective α-oxidation of acylpyrazoles

Seiya Taninokuchi, Ryo Yazaki, Takashi Ohshima

Research output: Contribution to journalArticlepeer-review

Abstract

Mechanistic studies on catalytic aerobic chemoselective α-oxidation of acylpyrazoles, including control experiments, kinetic isotope effect experiments, and radical clock experiments, are described. The key to promoting the reaction was the in-situ generation of a copper(II) peroxo complex, which serves as a Lewis acid/Brønsted base cooperative catalyst for efficient enolization. The present catalysis was applicable to late-stage α-oxidation of functionalized acylpyrazoles. A preliminary diastereoselective reaction using readily available chiral acylpyrazoles demonstrated that the present catalysis provided access to optically active α-hydroxy acid derivatives.

Original languageEnglish
Pages (from-to)906-918
Number of pages13
JournalHeterocycles
Volume99
Issue number2
DOIs
Publication statusPublished - 2019

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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