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

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posted on 2023-10-02, 06:35 authored by Kazuhiro OKAMOTO, Yasushi IMADA, Naoki SHIDA, Yoshikazu KITANO, Mahito Atobe, Kazuhiro CHIBA

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.

Funding

Establishment of pharmaceutical molecule synthesis process based on spatiotemporal redox control of electrolyzed cation species

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Development of electrode mediator system using hypervalent compound aimed at green material synthesis

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Japan Society for the Promotion of Science

Elucidation of adhesion inhibitory activity expression mechanism by chemical biology approach

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Creation of multi-stage continuous reaction system based on flow electrolysis reaction that enables spatiotemporal control of active species

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Creation of flow micro-electrolytic synthesis technology aimed at automating organic synthesis reactions

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Establishing a complete chemical synthesis process to produce 10 trillion kinds of peptide oligomers in one container

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Establishment of systematic chemical synthetic method of element substitution type nucleic acid oligomer which becomes the next generation nucleic acid drug candidate

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Construction of innovative reaction process based on solid polymer electrolyte electrolysis technology

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Continuous dehydration condensation reaction by electron transfer control

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History

Corresponding author email address

chiba@cc.tuat.ac.jp

Copyright

© 2023 The Author(s).

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