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

[Image: see text] 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 cyclop...

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Autores principales: Rybicka-Jasińska, Katarzyna, Szeptuch, Zuzanna, Kubiszewski, Hubert, Kowaluk, Agnieszka
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9972478/
https://www.ncbi.nlm.nih.gov/pubmed/36786497
http://dx.doi.org/10.1021/acs.orglett.3c00121
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author Rybicka-Jasińska, Katarzyna
Szeptuch, Zuzanna
Kubiszewski, Hubert
Kowaluk, Agnieszka
author_facet Rybicka-Jasińska, Katarzyna
Szeptuch, Zuzanna
Kubiszewski, Hubert
Kowaluk, Agnieszka
author_sort Rybicka-Jasińska, Katarzyna
collection PubMed
description [Image: see text] 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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spelling pubmed-99724782023-03-01 Electrochemical Cycloaddition Reactions of Alkene Radical Cations: A Route toward Cyclopropanes and Cyclobutanes Rybicka-Jasińska, Katarzyna Szeptuch, Zuzanna Kubiszewski, Hubert Kowaluk, Agnieszka Org Lett [Image: see text] 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. American Chemical Society 2023-02-14 /pmc/articles/PMC9972478/ /pubmed/36786497 http://dx.doi.org/10.1021/acs.orglett.3c00121 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Rybicka-Jasińska, Katarzyna
Szeptuch, Zuzanna
Kubiszewski, Hubert
Kowaluk, Agnieszka
Electrochemical Cycloaddition Reactions of Alkene Radical Cations: A Route toward Cyclopropanes and Cyclobutanes
title Electrochemical Cycloaddition Reactions of Alkene Radical Cations: A Route toward Cyclopropanes and Cyclobutanes
title_full Electrochemical Cycloaddition Reactions of Alkene Radical Cations: A Route toward Cyclopropanes and Cyclobutanes
title_fullStr Electrochemical Cycloaddition Reactions of Alkene Radical Cations: A Route toward Cyclopropanes and Cyclobutanes
title_full_unstemmed Electrochemical Cycloaddition Reactions of Alkene Radical Cations: A Route toward Cyclopropanes and Cyclobutanes
title_short Electrochemical Cycloaddition Reactions of Alkene Radical Cations: A Route toward Cyclopropanes and Cyclobutanes
title_sort electrochemical cycloaddition reactions of alkene radical cations: a route toward cyclopropanes and cyclobutanes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9972478/
https://www.ncbi.nlm.nih.gov/pubmed/36786497
http://dx.doi.org/10.1021/acs.orglett.3c00121
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AT kubiszewskihubert electrochemicalcycloadditionreactionsofalkeneradicalcationsaroutetowardcyclopropanesandcyclobutanes
AT kowalukagnieszka electrochemicalcycloadditionreactionsofalkeneradicalcationsaroutetowardcyclopropanesandcyclobutanes

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