DOI: 10.1021/acs.orglett.6c02722 ISSN: 1523-7060

Electroreductive N-Debenzylation of Amines and Amide Derivatives in an Undivided Cell

Tianyi Zhang, Yi Wang, Hao Guo, Xin Li, Feng Han, Zihan Zhang, Weixiao Ji, He Huang, Chenghui Sun, Siping Pang

Abstract

Direct electroreductive N-debenzylation of structurally diverse N-benzyl compounds was achieved in an undivided cell using a magnesium anode and carbon-felt cathode. Amines, N-heterocycles, amides, carbamates, ureas, lactams, and cyclic ureas were converted to the corresponding N–H products at room temperature without palladium catalysts or H2. The protocol exhibits broad functional-group tolerance and chemoselectively cleaves benzylic C–N bonds while preserving carbonyl frameworks, enabling late-stage deprotection of densely functionalized bioactive-molecule derivatives.

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