Electrochemical aromatic C–H hydroxylation in continuous flow

The direct hydroxylation of arene C–H bonds is a highly sought-after transformation but remains an unsolved challenge due to the difficulty in efficient and regioselective C–H oxygenation and high reactivity of the phenolic products leading to overoxidation. Herein we report electrochemical C–H hydr...

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Autores principales: Long, Hao, Chen, Tian-Sheng, Song, Jinshuai, Zhu, Shaobin, Xu, Hai-Chao
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9270493/
https://www.ncbi.nlm.nih.gov/pubmed/35803941
http://dx.doi.org/10.1038/s41467-022-31634-4
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author Long, Hao
Chen, Tian-Sheng
Song, Jinshuai
Zhu, Shaobin
Xu, Hai-Chao
author_facet Long, Hao
Chen, Tian-Sheng
Song, Jinshuai
Zhu, Shaobin
Xu, Hai-Chao
author_sort Long, Hao
collection PubMed
description The direct hydroxylation of arene C–H bonds is a highly sought-after transformation but remains an unsolved challenge due to the difficulty in efficient and regioselective C–H oxygenation and high reactivity of the phenolic products leading to overoxidation. Herein we report electrochemical C–H hydroxylation of arenes in continuous flow for the synthesis of phenols. The method is characterized by broad scope (compatible with arenes of diverse electronic properties), mild conditions without any catalysts or chemical oxidants, and excellent scalability as demonstrated by the continuous production of 1 mol (204 grams) of one of the phenol products.
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spelling pubmed-92704932022-07-10 Electrochemical aromatic C–H hydroxylation in continuous flow Long, Hao Chen, Tian-Sheng Song, Jinshuai Zhu, Shaobin Xu, Hai-Chao Nat Commun Article The direct hydroxylation of arene C–H bonds is a highly sought-after transformation but remains an unsolved challenge due to the difficulty in efficient and regioselective C–H oxygenation and high reactivity of the phenolic products leading to overoxidation. Herein we report electrochemical C–H hydroxylation of arenes in continuous flow for the synthesis of phenols. The method is characterized by broad scope (compatible with arenes of diverse electronic properties), mild conditions without any catalysts or chemical oxidants, and excellent scalability as demonstrated by the continuous production of 1 mol (204 grams) of one of the phenol products. Nature Publishing Group UK 2022-07-08 /pmc/articles/PMC9270493/ /pubmed/35803941 http://dx.doi.org/10.1038/s41467-022-31634-4 Text en © The Author(s) 2022 https://creativecommons.org/licenses/by/4.0/Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) .
spellingShingle Article
Long, Hao
Chen, Tian-Sheng
Song, Jinshuai
Zhu, Shaobin
Xu, Hai-Chao
Electrochemical aromatic C–H hydroxylation in continuous flow
title Electrochemical aromatic C–H hydroxylation in continuous flow
title_full Electrochemical aromatic C–H hydroxylation in continuous flow
title_fullStr Electrochemical aromatic C–H hydroxylation in continuous flow
title_full_unstemmed Electrochemical aromatic C–H hydroxylation in continuous flow
title_short Electrochemical aromatic C–H hydroxylation in continuous flow
title_sort electrochemical aromatic c–h hydroxylation in continuous flow
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9270493/
https://www.ncbi.nlm.nih.gov/pubmed/35803941
http://dx.doi.org/10.1038/s41467-022-31634-4
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AT songjinshuai electrochemicalaromaticchhydroxylationincontinuousflow
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AT xuhaichao electrochemicalaromaticchhydroxylationincontinuousflow

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