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Electrochemical deconstructive functionalization of cycloalkanols via alkoxy radicals enabled by proton-coupled Electron transfer

Hareram, Mishra Deepak, El Gehani, Albara A. M. A., Harnedy, James, Seastram, Alex C., Jones, Andrew C., Burns, Matthew, Wirth, Thomas ORCID: https://orcid.org/0000-0002-8990-0667, Browne, Duncan L. and Morrill, Louis C. ORCID: https://orcid.org/0000-0002-6453-7531 2022. Electrochemical deconstructive functionalization of cycloalkanols via alkoxy radicals enabled by proton-coupled Electron transfer. Organic Letters 24 (21) , pp. 3890-3895. 10.1021/acs.orglett.2c01552

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Abstract

Herein, we report a new electrochemical method for alkoxy radical generation from alcohols using a proton-coupled electron transfer (PCET) approach, showcased via the deconstructive functionalization of cycloalkanols. The electrochemical method is applicable across a diverse array of substituted cycloalkanols, accessing a broad range of synthetically useful distally functionalized ketones. The orthogonal derivatization of the products has been demonstrated through chemoselective transformations, and the electrochemical process has been performed on a gram scale in continuous single-pass flow.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Cardiff Catalysis Institute (CCI)
Additional Information: Attribution 4.0 International (CC BY 4.0)
Publisher: American Chemical Society
ISSN: 1523-7060
Funders: EPSRC
Date of First Compliant Deposit: 27 June 2022
Date of Acceptance: 20 May 2022
Last Modified: 10 Nov 2022 11:31
URI: https://orca.cardiff.ac.uk/id/eprint/150824

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