Copper(I)-catalyzed oxidation of alkenes using molecular oxygen and hydroxylamines: Synthesis and reactivity of α-oxygenated ketones

Alexander A. Andia, Matthew R. Miner, Keith Woerpel

Research output: Contribution to journalArticle

Abstract

The copper(I)-catalyzed oxidation of alkenes with molecular oxygen and N-hydroxyphthalimide (NHPI) or N-hydroxybenzotriazole (HOBt) provided α-oxygenated ketones. The reaction proceeded under a balloon of O<inf>2</inf> at room temperature to furnish the dioxygenated products in 50-90% yield. These compounds, particularly the HOBt derivatives, can be further functionalized with phosphorus, nitrogen, and sulfur nucleophiles to give synthetically useful products.

Original languageEnglish (US)
Pages (from-to)2704-2707
Number of pages4
JournalOrganic Letters
Volume17
Issue number11
DOIs
StatePublished - Jun 5 2015

Fingerprint

Hydroxylamines
Nucleophiles
Molecular oxygen
Balloons
Alkenes
Ketones
Sulfur
ketones
Phosphorus
alkenes
Copper
Nitrogen
reactivity
Oxygen
Derivatives
copper
Oxidation
oxidation
Temperature
nucleophiles

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Copper(I)-catalyzed oxidation of alkenes using molecular oxygen and hydroxylamines : Synthesis and reactivity of α-oxygenated ketones. / Andia, Alexander A.; Miner, Matthew R.; Woerpel, Keith.

In: Organic Letters, Vol. 17, No. 11, 05.06.2015, p. 2704-2707.

Research output: Contribution to journalArticle

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