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

Org Lett

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.

Published: January 2023

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.

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http://dx.doi.org/10.1021/acs.orglett.2c04154DOI Listing

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