Nickel-catalyzed electrochemical Minisci acylation of aromatic N-heterocycles with α-keto acids via ligand-to-metal electron transfer pathway

[Display omitted] •The first example of Ni-catalyzed Minisci acylation reaction was developed.•This protocol avoids using external chemical oxidants.•A ligand-to-metal electron transfer process was observed. A nickel-catalyzed electrochemical methodology for the Minisci acylation of aromatic electro...

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Bibliographic Details
Published in:Journal of catalysis Vol. 381; pp. 38 - 43
Main Authors: Ding, Hang, Xu, Kun, Zeng, Cheng-Chu
Format: Journal Article
Language:English
Published: Elsevier Inc 01.01.2020
Subjects:
acylation
catalysts
catalytic activity
electrochemistry
electron transfer
Electrosynthesis
free radicals
heterocyclic nitrogen compounds
keto acids
Minisci acylation reactions
nickel
Nickel-catalysis
oxidants
voltammetry
α-Keto acid
Electrosynthesis
Minisci acylation reactions
Nickel-catalysis
α-Keto acid
ISSN:0021-9517, 1090-2694
Online Access:Get full text
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Summary:[Display omitted] •The first example of Ni-catalyzed Minisci acylation reaction was developed.•This protocol avoids using external chemical oxidants.•A ligand-to-metal electron transfer process was observed. A nickel-catalyzed electrochemical methodology for the Minisci acylation of aromatic electron-deficient heterocycles with α-keto acids has been developed. The reaction is performed in an undivided cell under constant current conditions, featuring broad scope of substrates and avoiding the conventional utilization of silver-based catalysts in conjunction with excess amount of oxidants. Cyclic voltammetric analysis disclosed that a ligand-to-metal electron transfer process may be involved in the generation of the key acyl radicals.
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ISSN:0021-9517
1090-2694
DOI:10.1016/j.jcat.2019.10.030