Electrosynthesis of Nitrogen-containing Compounds in Nitromethane-Lithium Perchlorate Electrolyte System

Herein, we summarize the electrosynthetic approach toward nitrogen-containing compounds using a nitromethane-lithium perchlorate (MeNO2-LiClO4) electrolyte system. The reactivity of anodically generated cationic intermediates was significantly enhanced in the MeNO2-LiClO4 electrolyte system due to its weak donating nature. This electrolyte promoted various glycosidation and dehydrogenative cross-coupling reactions, yielding N-, C-azanucleosides and (pyrrolo)phenanthridone alkaloids with high regio- and stereoselectivity.

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Journal
Journal of Synthetic Organic Chemistry Japan
Published
2025-07-01
DOI
https://doi.org/10.5059/yukigoseikyokaishi.83.627
Primary Topic
Chemical Synthesis and Characterization
Type
article
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article

Electrosynthesis of Nitrogen-containing Compounds in Nitromethane-Lithium Perchlorate Electrolyte System

Kazuhiro Okamoto, Kazuhiro Chiba
Journal of Synthetic Organic Chemistry Japan
Chemical Synthesis and Characterization
article

Electrosynthesis of Nitrogen-containing Compounds in Nitromethane-Lithium Perchlorate Electrolyte System

Kazuhiro Okamoto, Kazuhiro Chiba
article en

Abstract

Herein, we summarize the electrosynthetic approach toward nitrogen-containing compounds using a nitromethane-lithium perchlorate (MeNO2-LiClO4) electrolyte system. The reactivity of anodically generated cationic intermediates was significantly enhanced in the MeNO2-LiClO4 electrolyte system due to its weak donating nature. This electrolyte promoted various glycosidation and dehydrogenative cross-coupling reactions, yielding N-, C-azanucleosides and (pyrrolo)phenanthridone alkaloids with high regio- and stereoselectivity.

Journal of Synthetic Organic Chemistry JapanVol. 83(7)
University of Toyama (JP), Tokyo University of Agriculture and Technology (JP)
Clean water and sanitation
Openalex Percentile: Top 81%
Chemical Synthesis and Characterization
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Electrosynthesis of Nitrogen-containing Compounds in Nitromethane-Lithium Perchlorate Electrolyte System — Kazuhiro Okamoto, Kazuhiro Chiba · Journal of Synthetic Organic Chemistry Japan (2025) | TGRS Research Map | TGRS