Metal-Free Electrochemically Reductive Deuteration of C═N Bonds with D<sub>2</sub>O toward Deuterated Amines
Yang Fan, Wei Ou, Mengyin Chen, Yubing Liu, Bing Zhang, Wenqing Ruan, Chenliang Su
Abstract
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.
Topics & Concepts
ChemistryDeuteriumElectrochemistryCarbanionKinetic isotope effectCatalysisCombinatorial chemistryMoleculeMetalOrganic chemistryElectrodePhysical chemistryPhysicsQuantum mechanicsChemical Reactions and IsotopesAsymmetric Hydrogenation and CatalysisAmmonia Synthesis and Nitrogen Reduction