CO 2 Transient Promotion Function Enabled the Selective Electrochemical Transformation of Imines

An unprecedented transient promotion function (TPF) of CO in the electrochemical hydrogenation/deuteration of imines (especially α-iminonitriles) is reported. The TPF influence of CO results from the introduction of CO that disperses the negative charges of the imine radical anion intermediate. The...

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Bibliographic Details
Published in:Organic letters 2023-12, Vol.25 (51), p.9202-9206
Main Authors: Fan, Yuhang, Chen, Chao, Zhang, Zhanshuo, Meng, Xiaohan, Liu, Xiaonuo, Cao, Jun, Jiang, Yuan-Ye, Zhao, Yulei
Format: Article
Language:English
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Summary:An unprecedented transient promotion function (TPF) of CO in the electrochemical hydrogenation/deuteration of imines (especially α-iminonitriles) is reported. The TPF influence of CO results from the introduction of CO that disperses the negative charges of the imine radical anion intermediate. The resulting redistribution of electrons leads to a lower reduction potential of the CO -substituted imine radical anion and thus facilitates the succeeding one-electron reduction. CO is finally released via spontaneous decarboxylation to complete the transient promotion process.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c03813