Copper(I)-Catalyzed Oxidation of Alkenes Using Molecular Oxygen and Hydroxylamines: Synthesis and Reactivity of α‑Oxygenated Ketones

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,...

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Bibliographic Details
Published inOrganic letters Vol. 17; no. 11; pp. 2704 - 2707
Main Authors Andia, Alexander A., Miner, Matthew R., Woerpel, K. A.
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.06.2015
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ACTIVATION
AEROBIC DIOXYGENATION
HYDROXAMIC ACIDS
CATALYZED OXIDATION
HOMOLYTIC DECOMPOSITIONS
CHEMISTRY
N-HYDROXYPHTHALIMIDE
HYDROPEROXIDES
DIKETONES
METAL-FREE
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Summary: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.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b01120