Photoredox/Palladium-Catalyzed Reduction Alkylation of Imines and Ammonium Salts via Dual C–N Bond Cleavage

Here, we report a photoredox/palladium-catalyzed reduction alkylation of imines and ammonium salts via dual C-N cleavage. This reaction proceeds under mild, green, and operationally simple conditions, offering a broad scope of secondary amine compounds with alpha quaternary carbon. Mechanistic studies indicate that the α-amino carbanion, generated by a successive single-electron transfer process, is a key intermediate in photoredox/palladium catalysis.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-04-16
DOI
https://doi.org/10.1021/acs.joc.5c00098
Citations
1
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.94

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article

Photoredox/Palladium-Catalyzed Reduction Alkylation of Imines and Ammonium Salts via Dual C–N Bond Cleavage

Tao Ju, Jian Xiong, Chao‐Guo Yan, Ying Han et al.
1 citations
The Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
0.94
article

Photoredox/Palladium-Catalyzed Reduction Alkylation of Imines and Ammonium Salts via Dual C–N Bond Cleavage

Tao Ju, Jian Xiong, Chao‐Guo Yan, Ying Han, Kun Huang, Jing Sun, Zhi‐Hao Wang, Ai-Ling Lu
article en
1 citations

Abstract

Here, we report a photoredox/palladium-catalyzed reduction alkylation of imines and ammonium salts via dual C-N cleavage. This reaction proceeds under mild, green, and operationally simple conditions, offering a broad scope of secondary amine compounds with alpha quaternary carbon. Mechanistic studies indicate that the α-amino carbanion, generated by a successive single-electron transfer process, is a key intermediate in photoredox/palladium catalysis.

The Journal of Organic ChemistryVol. 90(16)
Kanion Pharmaceutical (China) (CN), Taiwan Centers for Disease Control (TW), Yangzhou University (CN)
National Natural Science Foundation of China, China Postdoctoral Science Foundation, Natural Science Foundation of Jiangsu Province, Natural Science Research of Jiangsu Higher Education Institutions of China
Zero hunger
Openalex Percentile: Top 27%
Catalytic C–H Functionalization Methods
0.94
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