Metal-Free Electrochemically Reductive Deuteration of C═N Bonds with D 2 O toward Deuterated Amines

作者：Yang Fan, Wei Ou, Mengyin Chen, Yubing Liu, Bing Zhang, Wenqing Ruan, Chenliang Su · 发表于：Organic Letters · 年份：2023 · DOI：10.1021/acs.orglett.2c04154 · 被引用次数：32 · 研究领域：Chemical Reactions and Isotopes、Asymmetric Hydrogenation and Catalysis、Ammonia Synthesis and Nitrogen Reduction

Environmentally friendly and highly efficient synthesis of α-deuterated amines is achieved via a concise electrochemical process using D 2 O 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.