TCCA/RSeSeR 通过自由基过程介导的烯酰胺硒烷氧基化：硒基烯丙基 N,O-氨基的合成

IF 3.3 2区化学 Q1 CHEMISTRY, ORGANIC The Journal of Organic Chemistry Pub Date : 2024-10-18 DOI:10.1021/acs.joc.4c01601

Qingsong Liu, Jiri Gele, Kun Zhao, Shuting Zhang, Wen Gu, Zhigang Zhao, Xiaoxiao Li

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引用次数: 0

摘要

本研究开发了一种高效的 TCCA（三氯异氰尿酸）/RSeSeR 介导的硒烷氧基化荃酰胺，用于构建硒烯丙基 N,OA-氨基衍生物。该反应具有良好的官能团耐受性和高效性，能以良好至极佳的收率获得产物。机理研究表明，硒酰-烯丙基自由基中间体首先是通过添加到烯丙基酰胺中心碳上的 RSe 自由基形成的，随后通过氯自由基抽取电子生成高度稳定的硒酰-烯丙基碳位中间体。此外，这是首次报道使用硒试剂（RSeCl）通过自由基过程活化烯酰胺。

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TCCA/RSeSeR-Mediated Selenoalkoxy of Allenamides via a Radical Process: Synthesis of Selanyl-allylic N,O-Aminals

An efficient TCCA (trichloroisocyanuric acid)/RSeSeR-mediated selenoalkoxy of allenamides for the construction of selanyl-allylic N,OA-aminal derivatives was developed. The reaction exhibits good functional group tolerance and high efficiency, affording the products in good to excellent yields. Mechanistic investigations indicated that a selanyl-allylic radical intermediate was first formed via the RSe radical added to the central carbon of allenamides, which subsequently furnished highly stable selanyl-allylic carbocation intermediate by abstraction of an electron by the chlorine radical. Moreover, this is the first report of using selenium reagent (RSeCl) to activate allenamides via a radical process.

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来源期刊

The Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： The Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.