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

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.

SUBMITTER: Rybicka-Jasinska K

PROVIDER: S-EPMC9972478 | biostudies-literature | 2023 Feb

REPOSITORIES: biostudies-literature

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

Rybicka-Jasińska Katarzyna K Szeptuch Zuzanna Z Kubiszewski Hubert H Kowaluk Agnieszka A

Organic letters 20230214 7

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. ...[more]

PMID: 36786497

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