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

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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container_end_page 3895
container_issue 21
container_start_page 3890
container_title Organic letters
container_volume 24
creator 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.
description 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.
doi_str_mv 10.1021/acs.orglett.2c01552
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title Electrochemical Deconstructive Functionalization of Cycloalkanols via Alkoxy Radicals Enabled by Proton-Coupled Electron Transfer
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