Photocatalytic Pyridyl-carbamoylation of Alkenes for Accessing β-Pyridyl Amides

IF 5 1区 化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2025-03-07 DOI:10.1021/acs.orglett.5c00195
Cui Jian, Zhikai Li, Yuyuan Mao, Yilin Zhu, Weijie Yu, Jie Wu, Shaoyu Li
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Abstract

The β-pyridyl amide is a critical scaffold in medical discovery yet lacks efficient synthetic methods. Here, we describe, for the first time, a visible-light-induced, redox-neutral radical cross-coupling reaction involving alkenes, oxamic acids, and cyanopyridines that offers a versatile assembly of β-pyridylamides. This approach features mild reaction conditions, high step efficiency, and substrate breadth, providing a green and efficient strategy for alkene pyridyl-carbamoylation. Achieving this transformation relies on the efficient catalytic system, which adeptly avoids the competing cross-coupling of the nucleophilic carbamoyl radical with the electrophilic pyridyl radical, enabling the three-component radical tandem reaction process with high chemoselectivity.

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烯烃的光催化吡啶氨基化反应制备β-吡啶酰胺
β-吡啶酰胺是医学发现中的重要支架,但缺乏有效的合成方法。在这里,我们首次描述了一种可见光诱导的氧化还原中性自由基交叉偶联反应,涉及烯烃、肟酸和氰吡啶,提供了一种多功能的β-吡啶酰胺组装。该方法具有反应条件温和、台阶效率高、底物宽度宽等特点,为烯烃吡啶氨基甲酰化提供了一种绿色高效的方法。实现这一转化依赖于高效的催化体系,该体系巧妙地避免了亲核氨基甲酰自由基与亲电吡啶基自由基的竞争性交叉偶联,使三组分自由基串联反应过程具有较高的化学选择性。
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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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