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Photoelectrochemical oxidative C(sp(3))−H borylation of unactivated hydrocarbons
Organoboron compounds are of high significance in organic synthesis due to the unique versatility of boryl substituents to access further modifications. The high demand for the incorporation of boryl moieties into molecular structures has witnessed significant progress, particularly in the C(sp(3))−...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Nature Publishing Group UK
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10579347/ https://www.ncbi.nlm.nih.gov/pubmed/37845202 http://dx.doi.org/10.1038/s41467-023-42264-9 |
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author | Zhong, Ping-Fu Tu, Jia-Lin Zhao, Yating Zhong, Nan Yang, Chao Guo, Lin Xia, Wujiong |
author_facet | Zhong, Ping-Fu Tu, Jia-Lin Zhao, Yating Zhong, Nan Yang, Chao Guo, Lin Xia, Wujiong |
author_sort | Zhong, Ping-Fu |
collection | PubMed |
description | Organoboron compounds are of high significance in organic synthesis due to the unique versatility of boryl substituents to access further modifications. The high demand for the incorporation of boryl moieties into molecular structures has witnessed significant progress, particularly in the C(sp(3))−H borylation of hydrocarbons. Taking advantage of special characteristics of photo/electrochemistry, we herein describe the development of an oxidative C(sp(3))−H borylation reaction under metal- and oxidant-free conditions, enabled by photoelectrochemical strategy. The reaction exhibits broad substrate scope (>57 examples), and includes the use of simple alkanes, halides, silanes, ketones, esters and nitriles as viable substrates. Notably, unconventional regioselectivity of C(sp(3))−H borylation is achieved, with the coupling site of C(sp(3))−H borylation selectively located in the distal methyl group. Our method is operationally simple and easily scalable, and offers a feasible approach for the one-step synthesis of high-value organoboron building blocks from simple hydrocarbons, which would provide ample opportunities for drug discovery. |
format | Online Article Text |
id | pubmed-10579347 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | Nature Publishing Group UK |
record_format | MEDLINE/PubMed |
spelling | pubmed-105793472023-10-18 Photoelectrochemical oxidative C(sp(3))−H borylation of unactivated hydrocarbons Zhong, Ping-Fu Tu, Jia-Lin Zhao, Yating Zhong, Nan Yang, Chao Guo, Lin Xia, Wujiong Nat Commun Article Organoboron compounds are of high significance in organic synthesis due to the unique versatility of boryl substituents to access further modifications. The high demand for the incorporation of boryl moieties into molecular structures has witnessed significant progress, particularly in the C(sp(3))−H borylation of hydrocarbons. Taking advantage of special characteristics of photo/electrochemistry, we herein describe the development of an oxidative C(sp(3))−H borylation reaction under metal- and oxidant-free conditions, enabled by photoelectrochemical strategy. The reaction exhibits broad substrate scope (>57 examples), and includes the use of simple alkanes, halides, silanes, ketones, esters and nitriles as viable substrates. Notably, unconventional regioselectivity of C(sp(3))−H borylation is achieved, with the coupling site of C(sp(3))−H borylation selectively located in the distal methyl group. Our method is operationally simple and easily scalable, and offers a feasible approach for the one-step synthesis of high-value organoboron building blocks from simple hydrocarbons, which would provide ample opportunities for drug discovery. Nature Publishing Group UK 2023-10-16 /pmc/articles/PMC10579347/ /pubmed/37845202 http://dx.doi.org/10.1038/s41467-023-42264-9 Text en © The Author(s) 2023 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 licence, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons licence 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 licence, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) . |
spellingShingle | Article Zhong, Ping-Fu Tu, Jia-Lin Zhao, Yating Zhong, Nan Yang, Chao Guo, Lin Xia, Wujiong Photoelectrochemical oxidative C(sp(3))−H borylation of unactivated hydrocarbons |
title | Photoelectrochemical oxidative C(sp(3))−H borylation of unactivated hydrocarbons |
title_full | Photoelectrochemical oxidative C(sp(3))−H borylation of unactivated hydrocarbons |
title_fullStr | Photoelectrochemical oxidative C(sp(3))−H borylation of unactivated hydrocarbons |
title_full_unstemmed | Photoelectrochemical oxidative C(sp(3))−H borylation of unactivated hydrocarbons |
title_short | Photoelectrochemical oxidative C(sp(3))−H borylation of unactivated hydrocarbons |
title_sort | photoelectrochemical oxidative c(sp(3))−h borylation of unactivated hydrocarbons |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10579347/ https://www.ncbi.nlm.nih.gov/pubmed/37845202 http://dx.doi.org/10.1038/s41467-023-42264-9 |
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