A Mild Method for Electrochemical Reduction of Heterocyclic N‐Oxides

Deoxygenation of heteroaromatic N‐oxides is commonly accomplished using chemical or enzymatic methods. In this work, we report on an expedient protocol for electrochemical reduction of pyridine N‐oxide derivatives under mild conditions. A diverse range of mono‐ and bis N‐oxides were converted into t...

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Bibliographic Details
Published in:European journal of organic chemistry 2020-06, Vol.2020 (22), p.3317-3319
Main Authors: Fukazawa, Yasuaki, Rubtsov, Aleksandr E., Malkov, Andrei V.
Format: Article
Language:English
Subjects:
Chemical reduction
Deoxygenation
Electrochemistry
N ligands
Nitrogen
Nitrogen heterocycles
Oxides
Reduction
Synthetic methods
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Summary:Deoxygenation of heteroaromatic N‐oxides is commonly accomplished using chemical or enzymatic methods. In this work, we report on an expedient protocol for electrochemical reduction of pyridine N‐oxide derivatives under mild conditions. A diverse range of mono‐ and bis N‐oxides were converted into the corresponding nitrogen bases in good yields. Importantly, the method is highly selective towards N‐oxides and tolerates challenging halo and nitro substituents in the heteroaromatic ring. Deoxygenation of heteroaromatic N‐oxides is commonly accomplished using chemical or enzymatic methods. This work presents an expedient protocol for electrochemical reduction of pyridine N‐oxide derivatives under mild conditions. A range of mono‐ and bis N‐oxides were converted into the corresponding nitrogen bases in good yields. Importantly, N‐oxides are selectively reduced in the presence of halo and nitro substituents in the heteroaromatic ring.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202000377