Electrochemical difunctionalization of alkenes via chemoselective oxo-amination to access α-sulfonylamino ketones

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications Pub Date : 2026-04-03 Epub Date: 2026-03-19 DOI:10.1080/00397911.2026.2646265

Yu Liu (Validation) , Xiufeng Zhang (Formal analysis) , Zhangyang Shen (Data curation) , Xinyu Bu (Investigation) , Yingying Deng (Methodology) , Shengjun Li (Investigation) , Huanwen Chen (Supervision) , Pingnan Wan (Data curation) , Yang Wan (Supervision) , Sheng Zhang Liu (Writing – original draft Writing – review & editing)

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引用次数: 0

Abstract

The oxo-amination of alkenes represents a straightforward route to prepare α-amino ketones, which are valuable scaffolds for organic synthesis. The development of a practical method for this transformation is therefore actively being pursued. Herein, we report an electro-oxidative oxo-amination of alkenes that employs readily available O₂ as a green oxygen source, eliminating the need for an external oxidant. This strategy features a simple setup, broad substrate scope, mild conditions, and high atom economy, enabling the conversion of amines into diversely functionalized α-sulfonylamino ketones. Furthermore, the method was applied to the synthesis of the natural product halostachine. Mechanistic studies suggest a pathway initiated by the electrochemical generation of nitrogen-centred radicals, which subsequently add to alkenes.

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通过化学选择性氧胺化反应得到α-磺酰胺酮的烯烃电化学二官能化反应

烯烃的氧胺化反应是制备α-氨基酮的直接途径，是有机合成中有价值的支架材料。因此，正在积极谋求为这种转变发展一种实际的方法。在这里，我们报告了一种烯烃的电氧化氧胺化，它利用现成的O2作为绿色氧源，消除了对外部氧化剂的需要。该策略具有设置简单，底物范围广，条件温和，原子经济性高的特点，可以将胺转化为各种功能化的α-磺基胺酮。并将该方法应用于天然产物盐藻碱的合成。机理研究提出了一种由电化学生成氮中心自由基引发的途径，这些自由基随后加入到烯烃中。

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来源期刊

Synthetic Communications 化学-有机化学

CiteScore

4.40

自引率

4.80%

发文量

156

审稿时长

4.3 months

期刊介绍： Synthetic Communications presents communications describing new methods, reagents, and other synthetic work pertaining to organic chemistry with sufficient experimental detail to permit reported reactions to be repeated by a chemist reasonably skilled in the art. In addition, the Journal features short, focused review articles discussing topics within its remit of synthetic organic chemistry.