Electrochemistry
Online ISSN : 2186-2451
Print ISSN : 1344-3542
ISSN-L : 1344-3542

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UNCORRECTED PROOF
Mechanistic Insights into Electrooxidative Allylation of a Carbamate in the Presence of Solid-Supported Acids
Haruka HOMMANatsumi HONJOAkihiro TAKABAYASHIToshiki TAJIMA
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JOURNAL OPEN ACCESS Advance online publication
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Article ID: 25-00070

UNCORRECTED PROOF: May 23, 2025
ACCEPTED MANUSCRIPT: May 08, 2025
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Abstract

The electrooxidative allylation of a carbamate was successfully demonstrated using 3-propylsulfonic acid-functionalized silica gel (Si-SCX-2). It was shown that the electrochemical oxidation of the carbamate as a first step yields the corresponding N-acyliminium ion equivalent at room temperature, and the reaction of the N-acyliminium ion equivalent with allyltrimethylsilane as a next step leads to allylation without the use of Lewis acids. It was also found that the HBF4 generated by the cation exchange reaction between the Si-SCX-2 and the supporting electrolyte plays an important role in this reaction system.

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© The Author(s) 2025. Published by ECSJ.

This is an open access article distributed under the terms of the Creative Commons Attribution-NonCommercial-ShareAlike 4.0 License (CC BY-NC-SA, https://creativecommons.org/licenses/by-nc-sa/4.0/), which permits non-commercial reuse, distribution, and reproduction in any medium by share-alike, provided the original work is properly cited. For permission for commercial reuse, please email to the corresponding author. [DOI: 10.5796/electrochemistry.25-00070].
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