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

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

Research output: Contribution to journalArticlepeer-review

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 O2 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

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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