C–C Bond Cleavage at the N-α Position Enabled by the Low-potential Electrochemical Oxidation of the 2,7-Dimethoxynaphthyl Electroauxiliary

C–C Bond Cleavage at the N-α Position Enabled by the Low-potential Electrochemical Oxidation of the 2,7-Dimethoxynaphthyl Electroauxiliary

Herein, we report that the 2,7-dimethoxynaphthyl (2,7-DMN) group is a novel electroauxiliary that is readily installed at the N-α position of a carbamate through Friedel–Crafts-type arylation. The resulting N-α C–C bond is easily cleaved through low-potential electrochemical oxidation to give the co...

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Veröffentlicht in:Denki kagaku oyobi kōgyō butsuri kagaku 2023/11/28, Vol.91(11), pp.112006-112006
Hauptverfasser: OKAMOTO, Kazuhiro, IMADA, Yasushi, SHIDA, Naoki, KITANO, Yoshikazu, ATOBE, Mahito, CHIBA, Kazuhiro
Format: Artikel
Sprache:eng
Schlagworte:
Covalent bonds
Electroauxiliary
Electrochemical oxidation
Electrochemistry
Electrosynthesis
Iminium Cation
Oxidation
Radical Cation
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Beschreibung
Zusammenfassung:Herein, we report that the 2,7-dimethoxynaphthyl (2,7-DMN) group is a novel electroauxiliary that is readily installed at the N-α position of a carbamate through Friedel–Crafts-type arylation. The resulting N-α C–C bond is easily cleaved through low-potential electrochemical oxidation to give the corresponding iminium cation.
ISSN:1344-3542
2186-2451
DOI:10.5796/electrochemistry.23-67076