4.5 Article

A Mild Method for Electrochemical Reduction of Heterocyclic N-Oxides

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2020, Issue 22, Pages 3317-3319

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202000377

Keywords

Nitrogen heterocycles; Reduction; Electrochemistry; N ligands; Synthetic methods

Funding

  1. Russian Science Foundation [18-73-10156]
  2. Japanese Government
  3. Loughborough University
  4. Russian Science Foundation [18-73-10156] Funding Source: Russian Science Foundation

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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.

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