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Photocatalytic direct borylation of carboxylic acids
The preparation of high value-added boronic acids from cheap and plentiful carboxylic acids is desirable. To date, the decarboxylative borylation of carboxylic acids is generally realized through the extra step synthesized redox-active ester intermediate or in situ generated carboxylic acid covalent...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Nature Publishing Group UK
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9675845/ https://www.ncbi.nlm.nih.gov/pubmed/36402764 http://dx.doi.org/10.1038/s41467-022-34833-1 |
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author | Wei, Qiang Lee, Yuhsuan Liang, Weiqiu Chen, Xiaolei Mu, Bo-shuai Cui, Xi-Yang Wu, Wangsuo Bai, Shuming Liu, Zhibo |
author_facet | Wei, Qiang Lee, Yuhsuan Liang, Weiqiu Chen, Xiaolei Mu, Bo-shuai Cui, Xi-Yang Wu, Wangsuo Bai, Shuming Liu, Zhibo |
author_sort | Wei, Qiang |
collection | PubMed |
description | The preparation of high value-added boronic acids from cheap and plentiful carboxylic acids is desirable. To date, the decarboxylative borylation of carboxylic acids is generally realized through the extra step synthesized redox-active ester intermediate or in situ generated carboxylic acid covalent derivatives above 150 °C reaction temperature. Here, we report a direct decarboxylative borylation method of carboxylic acids enabled by visible-light catalysis and that does not require any extra stoichiometric additives or synthesis steps. This operationally simple process produces CO(2) and proceeds under mild reaction conditions, in terms of high step economy and good functional group compatibility. A guanidine-based biomimetic active decarboxylative mechanism is proposed and rationalized by mechanistic studies. The methodology reported herein should see broad application extending beyond borylation. |
format | Online Article Text |
id | pubmed-9675845 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | Nature Publishing Group UK |
record_format | MEDLINE/PubMed |
spelling | pubmed-96758452022-11-21 Photocatalytic direct borylation of carboxylic acids Wei, Qiang Lee, Yuhsuan Liang, Weiqiu Chen, Xiaolei Mu, Bo-shuai Cui, Xi-Yang Wu, Wangsuo Bai, Shuming Liu, Zhibo Nat Commun Article The preparation of high value-added boronic acids from cheap and plentiful carboxylic acids is desirable. To date, the decarboxylative borylation of carboxylic acids is generally realized through the extra step synthesized redox-active ester intermediate or in situ generated carboxylic acid covalent derivatives above 150 °C reaction temperature. Here, we report a direct decarboxylative borylation method of carboxylic acids enabled by visible-light catalysis and that does not require any extra stoichiometric additives or synthesis steps. This operationally simple process produces CO(2) and proceeds under mild reaction conditions, in terms of high step economy and good functional group compatibility. A guanidine-based biomimetic active decarboxylative mechanism is proposed and rationalized by mechanistic studies. The methodology reported herein should see broad application extending beyond borylation. Nature Publishing Group UK 2022-11-19 /pmc/articles/PMC9675845/ /pubmed/36402764 http://dx.doi.org/10.1038/s41467-022-34833-1 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 Wei, Qiang Lee, Yuhsuan Liang, Weiqiu Chen, Xiaolei Mu, Bo-shuai Cui, Xi-Yang Wu, Wangsuo Bai, Shuming Liu, Zhibo Photocatalytic direct borylation of carboxylic acids |
title | Photocatalytic direct borylation of carboxylic acids |
title_full | Photocatalytic direct borylation of carboxylic acids |
title_fullStr | Photocatalytic direct borylation of carboxylic acids |
title_full_unstemmed | Photocatalytic direct borylation of carboxylic acids |
title_short | Photocatalytic direct borylation of carboxylic acids |
title_sort | photocatalytic direct borylation of carboxylic acids |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9675845/ https://www.ncbi.nlm.nih.gov/pubmed/36402764 http://dx.doi.org/10.1038/s41467-022-34833-1 |
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