利用DO对C═N键进行无金属电化学还原氘代反应合成氘代胺类化合物
Metal-Free Electrochemically Reductive Deuteration of C═N Bonds with DO toward Deuterated Amines.
作者信息
Fan Yang, Ou Wei, Chen Mengyin, Liu Yubing, Zhang Bing, Ruan Wenqing, Su Chenliang
机构信息
International Collaborative Laboratory of 2D Materials for Optoelectronics Science and Technology of Ministry of Education, Institute of Microscale Optoelectronics, Shenzhen University, Shenzhen 518060, P. R. China.
School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, P. R. China.
出版信息
Org Lett. 2023 Jan 20;25(2):432-437. doi: 10.1021/acs.orglett.2c04154. Epub 2023 Jan 6.
Environmentally friendly and highly efficient synthesis of α-deuterated amines is achieved via a concise electrochemical process using DO as deuterium source without any external reductants or catalysts. Various imines are compatible, affording the desired products in high yields and D-incorporation. Gram-scale synthesis and flow-cell electrochemistry technology are used to synthesize deuterated pharmaceutical amines and their intermediates. Mechanistic studies reveal a plausible process, including the formation of carbanion species followed by deuterium atom transfer.
通过使用重水（DO）作为氘源的简洁电化学过程，在无任何外部还原剂或催化剂的情况下，实现了环境友好且高效的α-氘代胺的合成。各种亚胺均适用，能以高产率和高氘掺入量得到所需产物。采用克级合成和流通池电化学技术来合成氘代药物胺及其中间体。机理研究揭示了一个合理的过程，包括碳负离子物种的形成以及随后的氘原子转移。
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