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电化学炔烃氧化断键构建α-羰基芳酰胺衍生物的研究

Electrochemical oxidative cleavage of activated alkynes: a direct approach to carboxamide

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【作者】 杨帆高梦杨桂春

【Author】 YANG Fan;GAO Meng;YANG Guichun;College of Chemistry and Chemical Engineering, Hubei University;

【通讯作者】 高梦;杨桂春;

【机构】 湖北大学化学化工学院

【摘要】 在电化学条件下进行亚硝基苯与缺电子炔烃的偶联反应,实现了碳碳三键的断裂并生成α-羰基芳酰胺。反应在阴极单电子还原产生亚硝基自由基,随后对炔烃进行自由基加成并通过分子内重排断键一步合成α-羰基芳酰胺。通过对反应机理进行研究,表明α-羰基芳酰胺的氧来自于氧气。反应过程中使用氧气球提供氧气,10 mA恒定电流进行电解。该方法条件温和,操作简单,无需添加金属催化剂和额外的添加剂,具有良好的底物适用范围。

【Abstract】 The coupling reaction of nitrosobenzene with electron-deficient alkynes under electrochemical conditions was reported. The carbon-carbon triple bond was broken and α-carbonyl aromatic amide was generated. The reaction produced nitroso radicals by cathodic single electron reduction, followed by free radical addition of alkynes and one-step synthesis of α-carbonyl aromatic amide by intramolecular rearrangement of bonds. Through the study of the reaction mechanism, it was shown that the oxygen of α-carbonyl aromatic amide came from oxygen. During the reaction, oxygen spheres were used to provide oxygen, and electrolysis was performed at a constant current of 10 mA to obtain α-carbonyl aromatic amide. For the method, it has mild conditions, simple operation, no need to add metal catalysts and additional additives, and has a good substrate scope.

【基金】 国家自然科学基金面上项目(22271085)资助
  • 【文献出处】 湖北大学学报(自然科学版) ,Journal of Hubei University(Natural Science) , 编辑部邮箱 ,2024年01期
  • 【分类号】O625.63
  • 【下载频次】18
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