康 · 学术 | Reaction of the Day No. 1743

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,* and Siping Pang*

School of Materials Science and Engineering, Beijing Institute of Technology, Beijing 100081, China.

—Org. Lett., 2026, 28,10277.

Recommended by Yuting Gao and Bing Han_ MC3

KEY WORDS: N-debenzylation, electron chemistry (反应类型),N-benzyl compounds (原料), amines, N?H products (产物), N-H (成键类型)

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.

Background & Work Design

Conditions Optimization

Substrates Scope (selected examples)

Application in Complex Substrates

Summary and Comments

The group of Pro. He Huang, Chenghui Sun and Siping Pang developed a direct electroreductive N-debenzylation of structurally diverse N-benzyl substrates in a simple undivided cell. Constant-current electrolysis using a magnesium anode and a carbon-felt cathode converted a broad range of N-benzyl amines, N-heterocycles, carboxamides, carbamates, ureas, lactams, and cyclic ureas to the corresponding N?H products at room temperature. Notably, N-benzyl amides and related carbonyl-containing substrates underwent selective benzylic C?N bond cleavage while retaining their carbonyl frameworks, and the method was further applied to the late-stage deprotection of complex bioactive-molecule derivatives. This work provides a practical and complementary approach to N-debenzylation through direct cathodic C?N bond cleavage.