Amide Synthesis from Thiocarboxylic Acids and Amines by Spontaneous Reaction and Electrosynthesis
Amide Synthesis from Thiocarboxylic Acids and Amines by Spontaneous Reaction and Electrosynthesis
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硫代羧酸和胺通过自发反应和电合成合成酰胺
DOI：
10.1002/cssc.201900814
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发表时间：
2019
期刊：
影响因子：
8.4
通讯作者：
Guan Zhi
中科院分区：
文献类型：
--
作者：
Tang Li;Matuska Jack H;Huang Yu Han;He Yan Hong;Guan Zhi
酰胺键的形成是化学中最重要的基本反应之一。发展了一种由硫代羧酸和胺构筑酰胺键的无催化剂方法。反应机理研究表明，二硫键是合成酰胺的关键中间体。硫代苯甲酸在空气中可以自动氧化成二硫化物，硫代脂肪酸可以电氧化成二硫化物，生成的二硫化物与胺反应生成相应的酰胺。该方法无需任何催化剂或活化剂，即可方便、高效地合成各种酰胺类化合物。生物活性化合物的成功合成也突显了这一策略在药物化学中的合成应用。
Amide bond formation is one of the most important basic reactions in chemistry. A catalyst‐free approach for constructing amide bonds from thiocarboxylic acids and amines was developed. The mechanistic studies showed that the disulfide was the key intermediate for this amide synthesis. Thiobenzoic acids could be automatically oxidized to disulfides in air, thioaliphatic acids could be electro‐oxidized to disulfides, and the resulting disulfides reacted with amines to give the corresponding amides. By this method, various amides could be easily synthesized in excellent yields without using any catalyst or activator. The successful synthesis of bioactive compounds also highlights the synthetic utility of this strategy in medicinal chemistry.