CuI-Catalyzed Synthesis of Propargyl Hydroperoxides Using Molecular Oxygen and Hydroxylamines

Matthew R. Miner, K. A. Woerpel

Research output: Contribution to journalArticle

Abstract

A CuI-catalyzed oxidation of enynes using N-hydroxybenzotriazole (HOBt) or N-hydroxyphthalimide (NHPI) with molecular oxygen has been developed to yield propargyl hydroperoxides. The reaction occurs under O2 at 0°C to afford hydroperoxides in 1-4 h. This method provides an alternative to H2O2 or tBuOOH by using molecular oxygen as the source of oxygen atoms. The resulting hydroperoxides can be protected prior to purification and converted into alkoxyamines upon treatment with hydrazine.

Original languageEnglish (US)
Pages (from-to)1860-1866
Number of pages7
JournalEuropean Journal of Organic Chemistry
Volume2016
Issue number10
DOIs
StatePublished - Apr 2016

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Keywords

  • Enynes
  • Oxidation
  • Peroxides

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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