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

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.