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

被引：78
作者：
Andia, Alexander A. [1 ]
Miner, Matthew R. [1 ]
Woerpel, K. A. [1 ]
机构：
[1] NYU, Dept Chem, New York, NY 10003 USA
来源：
ORGANIC LETTERS | 2015年 / 17卷 / 11期
基金：
美国国家科学基金会;
关键词：
CATALYZED OXIDATION; N-HYDROXYPHTHALIMIDE; METAL-FREE; HOMOLYTIC DECOMPOSITIONS; AEROBIC DIOXYGENATION; HYDROXAMIC ACIDS; ACTIVATION; HYDROPEROXIDES; CHEMISTRY; DIKETONES;
D O I：
10.1021/acs.orglett.5b01120
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The copper(I)-catalyzed oxidation of alkenes with molecular oxygen and N-hydroxyphthalimide (NHPI) or N-hydroxybenzotriazole (HOBt) provided alpha-oxygenated ketones. The reaction proceeded under a balloon of O-2 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.
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收藏
页码：2704 / 2707
页数：4
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