Electrochemical Cycloaddition Reactions of Alkene Radical Cations: A Route toward Cyclopropanes and Cyclobutanes

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Authors
Rybicka-Jasińska, Katarzyna ORCID logo 0000-0002-9018-7846
Szeptuch, Zuzanna
Kubiszewski, Hubert
Kowaluk, Agnieszka
Date
2023
Journal Title
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Volume Title
Publisher
American Chemical Society
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Creative Commons License
Creative Commons Attribution 4.0 International License
Abstract
Herein, we describe a mild and efficient electrochemical method for cycloaddition reactions of alkene radical cations. Anodic oxidation of olefins produces electrophilic alkene radical cations, which further react with either diazo compounds in a [2 + 1] cycloaddition toward cyclopropane synthesis, or styrene derivatives in a [2 + 2] cycloaddition producing cyclobutanes. Both processes are green, metal- and catalyst-free, and scalable and tolerate a broad range of electron-rich olefins.
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Citation
Org. Lett. 2023, 25, 7, 1142–1146 ; https://doi.org/10.1021/acs.orglett.3c00121
URI
https://open.icm.edu.pl/handle/123456789/24861
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