Mechanistic Insights into Electrooxidative Allylation of a Carbamate in the Presence of Solid-Supported Acids
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, a...
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The Electrochemical Society of Japan
2025-06-01
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| Series: | Electrochemistry |
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| Online Access: | https://www.jstage.jst.go.jp/article/electrochemistry/93/6/93_25-00070/_html/-char/en |
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| author | Haruka HOMMA Natsumi HONJO Akihiro TAKABAYASHI Toshiki TAJIMA |
| author_facet | Haruka HOMMA Natsumi HONJO Akihiro TAKABAYASHI Toshiki TAJIMA |
| author_sort | Haruka HOMMA |
| collection | DOAJ |
| description | 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. |
| format | Article |
| id | doaj-art-b734124fae884ba8acf8486cb2a4e110 |
| institution | OA Journals |
| issn | 2186-2451 |
| language | English |
| publishDate | 2025-06-01 |
| publisher | The Electrochemical Society of Japan |
| record_format | Article |
| series | Electrochemistry |
| spelling | doaj-art-b734124fae884ba8acf8486cb2a4e1102025-08-20T02:10:25ZengThe Electrochemical Society of JapanElectrochemistry2186-24512025-06-0193606700306700310.5796/electrochemistry.25-00070electrochemistryMechanistic Insights into Electrooxidative Allylation of a Carbamate in the Presence of Solid-Supported AcidsHaruka HOMMA0https://orcid.org/0009-0005-0854-5261Natsumi HONJO1Akihiro TAKABAYASHI2Toshiki TAJIMA3https://orcid.org/0009-0000-8933-1225Graduate School of Engineering and Science, Shibaura Institute of TechnologyGraduate School of Engineering and Science, Shibaura Institute of TechnologyGraduate School of Engineering and Science, Shibaura Institute of TechnologyGraduate School of Engineering and Science, Shibaura Institute of TechnologyThe 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.https://www.jstage.jst.go.jp/article/electrochemistry/93/6/93_25-00070/_html/-char/enelectrooxidative allylationn-acyliminium ionsolid-supported acidcation exchange reaction |
| spellingShingle | Haruka HOMMA Natsumi HONJO Akihiro TAKABAYASHI Toshiki TAJIMA Mechanistic Insights into Electrooxidative Allylation of a Carbamate in the Presence of Solid-Supported Acids Electrochemistry electrooxidative allylation n-acyliminium ion solid-supported acid cation exchange reaction |
| title | Mechanistic Insights into Electrooxidative Allylation of a Carbamate in the Presence of Solid-Supported Acids |
| title_full | Mechanistic Insights into Electrooxidative Allylation of a Carbamate in the Presence of Solid-Supported Acids |
| title_fullStr | Mechanistic Insights into Electrooxidative Allylation of a Carbamate in the Presence of Solid-Supported Acids |
| title_full_unstemmed | Mechanistic Insights into Electrooxidative Allylation of a Carbamate in the Presence of Solid-Supported Acids |
| title_short | Mechanistic Insights into Electrooxidative Allylation of a Carbamate in the Presence of Solid-Supported Acids |
| title_sort | mechanistic insights into electrooxidative allylation of a carbamate in the presence of solid supported acids |
| topic | electrooxidative allylation n-acyliminium ion solid-supported acid cation exchange reaction |
| url | https://www.jstage.jst.go.jp/article/electrochemistry/93/6/93_25-00070/_html/-char/en |
| work_keys_str_mv | AT harukahomma mechanisticinsightsintoelectrooxidativeallylationofacarbamateinthepresenceofsolidsupportedacids AT natsumihonjo mechanisticinsightsintoelectrooxidativeallylationofacarbamateinthepresenceofsolidsupportedacids AT akihirotakabayashi mechanisticinsightsintoelectrooxidativeallylationofacarbamateinthepresenceofsolidsupportedacids AT toshikitajima mechanisticinsightsintoelectrooxidativeallylationofacarbamateinthepresenceofsolidsupportedacids |