Electrochemical Deconstructive Functionalization of Cycloalkanols via Alkoxy Radicals Enabled by Proton-Coupled Electron Transfer

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 cyc...

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Veröffentlicht in:Organic letters 2022-06, Vol.24 (21), p.3890-3895
Hauptverfasser: Hareram, Mishra Deepak, El Gehani, Albara A. M. A., Harnedy, James, Seastram, Alex C., Jones, Andrew C., Burns, Matthew, Wirth, Thomas, Browne, Duncan L., Morrill, Louis C.
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Sprache:eng
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c01552