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

Kazuhiro OKAMOTO; Yasushi IMADA; Naoki SHIDA; Yoshikazu KITANO; Mahito ATOBE; Kazuhiro CHIBA

doi:10.5796/electrochemistry.23-67076

This article has now been updated. Please use the final version.

UNCORRECTED PROOF

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

Kazuhiro OKAMOTO, Yasushi IMADA, Naoki SHIDA, Yoshikazu KITANO, Mahito ATOBE, Kazuhiro CHIBA

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Keywords: Electrosynthesis, Electroauxiliary, Radical Cation, Iminium Cation

JOURNAL OPEN ACCESS Advance online publication
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Article ID: 23-67076

DOI https://doi.org/10.5796/electrochemistry.23-67076

The final version of this article is now available: Vol. 91 (2023), No. 11 pp. 112006-112006

UNCORRECTED PROOF： October 03, 2023
ACCEPTED MANUSCRIPT： September 13, 2023

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Abstract

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.

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