General and versatile electrochemical α-C(sp<sup>3</sup>)–H amidation for <i>N</i>-Mannich base synthesis

A green and versatile electrochemical method for the synthesis of <i>N</i>-Mannich bases through oxidative dehydrogenative cross-coupling is reported. A wide range of primary amides, lactams and phthalimides serve as effective amidation reagents, enabling the α-functionalization of both aromatic and aliphatic tertiary amines with excellent regioselectivity and high efficiency under mild, metal-/oxidant-free conditions. This sustainable approach is characterized by its operational-simplicity, broad substrate compatibility, and exceptional functional group tolerance. The practicality and utility of the method are demonstrated by its easy scalability and late-stage modification of structural complex molecules.

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Publication Details

Journal
Chemical Communications
Published
2025-01-01
DOI
https://doi.org/10.1039/d5cc03433g
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.00

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article

General and versatile electrochemical α-C(sp3)–H amidation for N-Mannich base synthesis

R. Zhou, Jian Wang, Ting Li, Ming Chen et al.
Chemical Communications
Catalytic C–H Functionalization Methods
article

General and versatile electrochemical α-C(sp3)–H amidation for N-Mannich base synthesis

R. Zhou, Jian Wang, Ting Li, Ming Chen, Yiming Liu, Wenguang Li, Chunxia Yang, Xinxin Zhao, Mengxin Qu, Jiahui Zheng
article en

Abstract

A green and versatile electrochemical method for the synthesis of <i>N</i>-Mannich bases through oxidative dehydrogenative cross-coupling is reported. A wide range of primary amides, lactams and phthalimides serve as effective amidation reagents, enabling the α-functionalization of both aromatic and aliphatic tertiary amines with excellent regioselectivity and high efficiency under mild, metal-/oxidant-free conditions. This sustainable approach is characterized by its operational-simplicity, broad substrate compatibility, and exceptional functional group tolerance. The practicality and utility of the method are demonstrated by its easy scalability and late-stage modification of structural complex molecules.

Chemical CommunicationsVol. 61(67)
Nanyang Normal University (CN)
National Natural Science Foundation of China, Nanyang Normal University
Openalex Percentile: Top 87%
Catalytic C–H Functionalization Methods
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General and versatile electrochemical α-C(sp<sup>3</sup>)–H amidation for <i>N</i>-Mannich base synthesis — R. Zhou, Jian Wang, et al. · Chemical Communications (2025) | TGRS Research Map | TGRS