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

Matthew R. Miner, Keith 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 1 2016

Fingerprint

Hydroxylamines
Molecular oxygen
Hydrogen Peroxide
hydrazine
hydrazines
oxygen
synthesis
purification
oxygen atoms
oxidation
Purification
Oxygen
Atoms
Oxidation

Keywords

  • Enynes
  • Oxidation
  • Peroxides

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry

Cite this

CuI-Catalyzed Synthesis of Propargyl Hydroperoxides Using Molecular Oxygen and Hydroxylamines. / Miner, Matthew R.; Woerpel, Keith.

In: European Journal of Organic Chemistry, Vol. 2016, No. 10, 01.04.2016, p. 1860-1866.

Research output: Contribution to journalArticle

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