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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...

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Detalles Bibliográficos
Autores principales: Lu, Sixian, Chen, Xingyu, Chang, Xiaoqiang, Zhang, Shuaichen, Zhang, Dong, Zhao, Yifan, Yang, Lan, Ma, Yue, Sun, Peng
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
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.
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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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