Deconstructive Functionalization of Unstrained Cycloalkanols via Electrochemically Generated Aromatic Radical Cations

[Image: see text] Herein we report an electrochemical approach for the deconstructive functionalization of cycloalkanols, where various alcohols, carboxylic acids, and N-heterocycles are employed as nucleophiles. The method has been demonstrated across a broad range of cycloalkanol substrates, inclu...

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Autores principales: Harnedy, James, Maashi, Hussain A., El Gehani, Albara A. M. A., Burns, Matthew, Morrill, Louis C.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10012273/
https://www.ncbi.nlm.nih.gov/pubmed/36847269
http://dx.doi.org/10.1021/acs.orglett.3c00219
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author Harnedy, James
Maashi, Hussain A.
El Gehani, Albara A. M. A.
Burns, Matthew
Morrill, Louis C.
author_facet Harnedy, James
Maashi, Hussain A.
El Gehani, Albara A. M. A.
Burns, Matthew
Morrill, Louis C.
author_sort Harnedy, James
collection PubMed
description [Image: see text] Herein we report an electrochemical approach for the deconstructive functionalization of cycloalkanols, where various alcohols, carboxylic acids, and N-heterocycles are employed as nucleophiles. The method has been demonstrated across a broad range of cycloalkanol substrates, including various ring sizes and substituents, to access useful remotely functionalized ketone products (36 examples). The method was demonstrated on a gram scale via single-pass continuous flow, which exhibited increased productivity in relation to the batch process.
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spelling pubmed-100122732023-03-15 Deconstructive Functionalization of Unstrained Cycloalkanols via Electrochemically Generated Aromatic Radical Cations Harnedy, James Maashi, Hussain A. El Gehani, Albara A. M. A. Burns, Matthew Morrill, Louis C. Org Lett [Image: see text] Herein we report an electrochemical approach for the deconstructive functionalization of cycloalkanols, where various alcohols, carboxylic acids, and N-heterocycles are employed as nucleophiles. The method has been demonstrated across a broad range of cycloalkanol substrates, including various ring sizes and substituents, to access useful remotely functionalized ketone products (36 examples). The method was demonstrated on a gram scale via single-pass continuous flow, which exhibited increased productivity in relation to the batch process. American Chemical Society 2023-02-27 /pmc/articles/PMC10012273/ /pubmed/36847269 http://dx.doi.org/10.1021/acs.orglett.3c00219 Text en © 2023 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 Harnedy, James
Maashi, Hussain A.
El Gehani, Albara A. M. A.
Burns, Matthew
Morrill, Louis C.
Deconstructive Functionalization of Unstrained Cycloalkanols via Electrochemically Generated Aromatic Radical Cations
title Deconstructive Functionalization of Unstrained Cycloalkanols via Electrochemically Generated Aromatic Radical Cations
title_full Deconstructive Functionalization of Unstrained Cycloalkanols via Electrochemically Generated Aromatic Radical Cations
title_fullStr Deconstructive Functionalization of Unstrained Cycloalkanols via Electrochemically Generated Aromatic Radical Cations
title_full_unstemmed Deconstructive Functionalization of Unstrained Cycloalkanols via Electrochemically Generated Aromatic Radical Cations
title_short Deconstructive Functionalization of Unstrained Cycloalkanols via Electrochemically Generated Aromatic Radical Cations
title_sort deconstructive functionalization of unstrained cycloalkanols via electrochemically generated aromatic radical cations
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10012273/
https://www.ncbi.nlm.nih.gov/pubmed/36847269
http://dx.doi.org/10.1021/acs.orglett.3c00219
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