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Boron-catalysed transition-metal-free arylation and alkenylation of allylic alcohols with boronic acids
The development of efficient catalytic reactions with excellent atom and step economy employing sustainable catalysts is highly sought-after in chemical synthesis to reduce the negative effects on the environment. The most commonly-used strategy to construct allylic compounds relies on the transitio...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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The Royal Society of Chemistry
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9869934/ https://www.ncbi.nlm.nih.gov/pubmed/36756407 http://dx.doi.org/10.1039/d2ra07919d |
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author | Lu, Sixian Chen, Xingyu Chang, Xiaoqiang Zhang, Shuaichen Zhang, Dong Zhao, Yifan Yang, Lan Ma, Yue Sun, Peng |
author_facet | Lu, Sixian Chen, Xingyu Chang, Xiaoqiang Zhang, Shuaichen Zhang, Dong Zhao, Yifan Yang, Lan Ma, Yue Sun, Peng |
author_sort | Lu, Sixian |
collection | PubMed |
description | The development of efficient catalytic reactions with excellent atom and step economy employing sustainable catalysts is highly sought-after in chemical synthesis to reduce the negative effects on the environment. The most commonly-used strategy to construct allylic compounds relies on the transition-metal-catalysed nucleophilic substitution reaction of allylic alcohol derivatives. These syntheses exhibit good yield and selectivity, albeit at the expense of toxic and expensive catalysts and extra steps. In this paper, we report a transition-metal-free arylation and alkenylation reaction between unprotected allylic alcohols and boronic acids. The reactions were performed with B(C(6)F(5))(3) as the catalyst in toluene, and corresponding products were obtained in 23–92% yields. The reaction has mild conditions, scalability, excellent atom and step economy. |
format | Online Article Text |
id | pubmed-9869934 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-98699342023-02-07 Boron-catalysed transition-metal-free arylation and alkenylation of allylic alcohols with boronic acids Lu, Sixian Chen, Xingyu Chang, Xiaoqiang Zhang, Shuaichen Zhang, Dong Zhao, Yifan Yang, Lan Ma, Yue Sun, Peng RSC Adv Chemistry The development of efficient catalytic reactions with excellent atom and step economy employing sustainable catalysts is highly sought-after in chemical synthesis to reduce the negative effects on the environment. The most commonly-used strategy to construct allylic compounds relies on the transition-metal-catalysed nucleophilic substitution reaction of allylic alcohol derivatives. These syntheses exhibit good yield and selectivity, albeit at the expense of toxic and expensive catalysts and extra steps. In this paper, we report a transition-metal-free arylation and alkenylation reaction between unprotected allylic alcohols and boronic acids. The reactions were performed with B(C(6)F(5))(3) as the catalyst in toluene, and corresponding products were obtained in 23–92% yields. The reaction has mild conditions, scalability, excellent atom and step economy. The Royal Society of Chemistry 2023-01-23 /pmc/articles/PMC9869934/ /pubmed/36756407 http://dx.doi.org/10.1039/d2ra07919d Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/ |
spellingShingle | Chemistry Lu, Sixian Chen, Xingyu Chang, Xiaoqiang Zhang, Shuaichen Zhang, Dong Zhao, Yifan Yang, Lan Ma, Yue Sun, Peng Boron-catalysed transition-metal-free arylation and alkenylation of allylic alcohols with boronic acids |
title | Boron-catalysed transition-metal-free arylation and alkenylation of allylic alcohols with boronic acids |
title_full | Boron-catalysed transition-metal-free arylation and alkenylation of allylic alcohols with boronic acids |
title_fullStr | Boron-catalysed transition-metal-free arylation and alkenylation of allylic alcohols with boronic acids |
title_full_unstemmed | Boron-catalysed transition-metal-free arylation and alkenylation of allylic alcohols with boronic acids |
title_short | Boron-catalysed transition-metal-free arylation and alkenylation of allylic alcohols with boronic acids |
title_sort | boron-catalysed transition-metal-free arylation and alkenylation of allylic alcohols with boronic acids |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9869934/ https://www.ncbi.nlm.nih.gov/pubmed/36756407 http://dx.doi.org/10.1039/d2ra07919d |
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