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

  • OKAMOTO Kazuhiro
    Graduate School of Engineering, Yokohama National University
  • IMADA Yasushi
    Department of Applied Biological Science, Tokyo University of Agriculture and Technology
  • SHIDA Naoki
    Graduate School of Engineering, Yokohama National University
  • KITANO Yoshikazu
    Department of Applied Biological Science, Tokyo University of Agriculture and Technology
  • ATOBE Mahito
    Graduate School of Engineering, Yokohama National University
  • CHIBA Kazuhiro
    Department of Applied Biological Science, Tokyo University of Agriculture and Technology

Description

<p>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.</p>

Journal

  • Electrochemistry

    Electrochemistry 91 (11), 112006-112006, 2023-11-28

    The Electrochemical Society of Japan

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