Manganese-Promoted Electrochemical Imino-Pinacol Coupling to Access Vicinal Diamines

We herein introduce an electrochemical imino-pinacol coupling reaction to access the vicinal diamine scaffold. This green and convenient protocol employs in situ-generated imines as starting materials to deliver a broad range of diamine products under electroreductive conditions. Moreover, this protocol is also applicable to electrochemical pinacol coupling. Mechanistic investigation suggests that a Mn(III) additive is essential for promoting the SET reduction of the imine starting material and preventing the formation of the over-reduced amine side product.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-03-05
DOI
https://doi.org/10.1021/acs.joc.4c02994
Citations
3
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
2.81

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article

Manganese-Promoted Electrochemical Imino-Pinacol Coupling to Access Vicinal Diamines

Xiaolong Xu, Dong Wang, Yingqi Yang, Weihao Cui et al.
3 citations
The Journal of Organic Chemistry
Radical Photochemical Reactions
2.81
article

Manganese-Promoted Electrochemical Imino-Pinacol Coupling to Access Vicinal Diamines

Xiaolong Xu, Dong Wang, Yingqi Yang, Weihao Cui, Qiong Wang, Cong Zhang, Jin Wang
article en
3 citations

Abstract

We herein introduce an electrochemical imino-pinacol coupling reaction to access the vicinal diamine scaffold. This green and convenient protocol employs in situ-generated imines as starting materials to deliver a broad range of diamine products under electroreductive conditions. Moreover, this protocol is also applicable to electrochemical pinacol coupling. Mechanistic investigation suggests that a Mn(III) additive is essential for promoting the SET reduction of the imine starting material and preventing the formation of the over-reduced amine side product.

The Journal of Organic ChemistryVol. 90(10)
Shandong Normal University (CN)
National Natural Science Foundation of China
Openalex Percentile: Top 12%
Radical Photochemical Reactions
2.81
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Manganese-Promoted Electrochemical Imino-Pinacol Coupling to Access Vicinal Diamines — Xiaolong Xu, Dong Wang, et al. · The Journal of Organic Chemistry (2025) | TGRS Research Map | TGRS