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

[Image: see text] 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...

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Autores principales: 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.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9171832/
https://www.ncbi.nlm.nih.gov/pubmed/35604008
http://dx.doi.org/10.1021/acs.orglett.2c01552
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author 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.
author_facet 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.
author_sort Hareram, Mishra Deepak
collection PubMed
description [Image: see text] 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.
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spelling pubmed-91718322022-06-08 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. Morrill, Louis C. Org Lett [Image: see text] 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. American Chemical Society 2022-05-23 2022-06-03 /pmc/articles/PMC9171832/ /pubmed/35604008 http://dx.doi.org/10.1021/acs.orglett.2c01552 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle 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.
Electrochemical Deconstructive Functionalization of Cycloalkanols via Alkoxy Radicals Enabled by Proton-Coupled Electron Transfer
title Electrochemical Deconstructive Functionalization of Cycloalkanols via Alkoxy Radicals Enabled by Proton-Coupled Electron Transfer
title_full Electrochemical Deconstructive Functionalization of Cycloalkanols via Alkoxy Radicals Enabled by Proton-Coupled Electron Transfer
title_fullStr Electrochemical Deconstructive Functionalization of Cycloalkanols via Alkoxy Radicals Enabled by Proton-Coupled Electron Transfer
title_full_unstemmed Electrochemical Deconstructive Functionalization of Cycloalkanols via Alkoxy Radicals Enabled by Proton-Coupled Electron Transfer
title_short Electrochemical Deconstructive Functionalization of Cycloalkanols via Alkoxy Radicals Enabled by Proton-Coupled Electron Transfer
title_sort electrochemical deconstructive functionalization of cycloalkanols via alkoxy radicals enabled by proton-coupled electron transfer
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9171832/
https://www.ncbi.nlm.nih.gov/pubmed/35604008
http://dx.doi.org/10.1021/acs.orglett.2c01552
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