Copper-Catalyzed Oxidative α-Double Bond Construction in α-Amino Carbonyl Compounds via Homocoupling with Arylamine Release

IF 4.9 1区 化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2024-09-17 DOI:10.1021/acs.orglett.4c03044
Huan Wang, Yi-bin Wang, Yan-fang Zhan, Yi-ting Zhu, Yan Jiang, Sen Yang, Ming Chen
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Abstract

Herein, we present a copper-catalyzed method for oxidative α-double bond formation in α-amino ketone compounds using DTBP as the oxidant. This process, involving homocoupling of α-amino radicals and arylamine release, efficiently produces a series of enaminone skeletons. The strategy has a broad substrate scope and functional group tolerance. In particular, arylamines bearing electron-rich substituents exhibit a pronounced reactivity. This approach facilitates the synthesis of diverse enaminones, enabling the efficient construction of nitrogen-containing heterocycles.

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铜催化α-氨基羰基化合物通过释放芳胺的同偶联反应氧化α-双键结构
在此,我们提出了一种铜催化方法,以 DTBP 为氧化剂,在 α-氨基酮化合物中氧化形成 α-双键。这一过程涉及 α-氨基自由基的同偶联和芳基胺的释放,能有效地生成一系列烯酮骨架。该策略具有广泛的底物范围和官能团耐受性。尤其是带有富电子取代基的芳基胺具有明显的反应活性。这种方法有助于合成多种烯酮,从而高效地构建含氮杂环。
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来源期刊
Organic Letters
Organic Letters 化学-有机化学
CiteScore
9.30
自引率
11.50%
发文量
1607
审稿时长
1.5 months
期刊介绍: Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
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