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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, Browne, Duncan L. and Morrill, Louis C. 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: 30 Jun 2022 08:43
URI: https://orca.cardiff.ac.uk/id/eprint/150824

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