Electrochemical synthesis of C(sp 3 )‑rich heterocycles via mesolytic cleavage of anodically generated aromatic radical cations

Maashi, Hussain A., Husayni, Abdulrahman H., M, Kharou, Reid, Michael E., Harnedy, James, Herneman, Ethan C., Pera-Titus, Marc and Morrill, Louis C. ORCID: https://orcid.org/0000-0002-6453-7531 2024. Electrochemical synthesis of C(sp 3 )‑rich heterocycles via mesolytic cleavage of anodically generated aromatic radical cations. Organic Letters 26 (42) , pp. 9051-9055. 10.1021/acs.orglett.4c03091

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Abstract

Herein we report an electrochemical deconstructive functionalization approach for the synthesis of C­(sp3)-rich heterocycles. The reaction proceeds via the mesolytic cleavage of anodically generated aromatic radical cations and the trapping of formed carbocation intermediates with internal nucleophiles. The method has been demonstrated across various arylalcohol substrates to access a diverse range of C­(sp3)-rich heterocycles including tetrahydrofuran, tetrahydropyran, and pyrrolidine scaffolds (26 examples). The electrochemical method was demonstrated on a 5 mmol scale via single pass continuous flow, which utilized lower supporting electrolyte concentration and exhibited increased productivity in relation to the batch process.

Item Type:	Article
Date Type:	Published Online
Status:	Published
Schools:	Chemistry Cardiff Catalysis Institute (CCI)
Additional Information:	License information from Publisher: LICENSE 1: URL: https://creativecommons.org/licenses/by/4.0/, Start Date: 2024-10-21
Publisher:	American Chemical Society
ISSN:	1523-7060
Date of First Compliant Deposit:	29 October 2024
Date of Acceptance:	15 October 2024
Last Modified:	29 Oct 2024 10:30
URI:	https://orca.cardiff.ac.uk/id/eprint/173496

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