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Direct synthesis of sila-benzoazoles through hydrosilylation and rearrangement cascade reaction of benzoazoles and silanes

Sila-isosteres have attracted increasing attention due to their potential application in a variety of fields and their different properties compared to their carbon-containing analogs. However, the preparation of these silicon-containing compound remains challenging and thus the development of alter...

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Autores principales: Liu, Tianwei, Yang, Mo, He, Jianghua, Li, Shuhua, Zhang, Yuetao
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9911738/
https://www.ncbi.nlm.nih.gov/pubmed/36759604
http://dx.doi.org/10.1038/s41467-023-36360-z
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author Liu, Tianwei
Yang, Mo
He, Jianghua
Li, Shuhua
Zhang, Yuetao
author_facet Liu, Tianwei
Yang, Mo
He, Jianghua
Li, Shuhua
Zhang, Yuetao
author_sort Liu, Tianwei
collection PubMed
description Sila-isosteres have attracted increasing attention due to their potential application in a variety of fields and their different properties compared to their carbon-containing analogs. However, the preparation of these silicon-containing compound remains challenging and thus the development of alternative synthetic methodologies is desirable. Here, we employ B(C(6)F(5))(3) as catalyst to enable the synthesis of highly functionalized sila-benzoazoles via hydrosilylation and rearrangement cascade reaction of benzoazoles and commercially available silanes. This strategy also exhibits remarkable features such as 100% atom-economy, good functional group tolerance, broad substrate scope, easy scale-up and good catalytic performance, demonstrating its potential application in sila-isostere synthesis.
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spelling pubmed-99117382023-02-11 Direct synthesis of sila-benzoazoles through hydrosilylation and rearrangement cascade reaction of benzoazoles and silanes Liu, Tianwei Yang, Mo He, Jianghua Li, Shuhua Zhang, Yuetao Nat Commun Article Sila-isosteres have attracted increasing attention due to their potential application in a variety of fields and their different properties compared to their carbon-containing analogs. However, the preparation of these silicon-containing compound remains challenging and thus the development of alternative synthetic methodologies is desirable. Here, we employ B(C(6)F(5))(3) as catalyst to enable the synthesis of highly functionalized sila-benzoazoles via hydrosilylation and rearrangement cascade reaction of benzoazoles and commercially available silanes. This strategy also exhibits remarkable features such as 100% atom-economy, good functional group tolerance, broad substrate scope, easy scale-up and good catalytic performance, demonstrating its potential application in sila-isostere synthesis. Nature Publishing Group UK 2023-02-09 /pmc/articles/PMC9911738/ /pubmed/36759604 http://dx.doi.org/10.1038/s41467-023-36360-z 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 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
Liu, Tianwei
Yang, Mo
He, Jianghua
Li, Shuhua
Zhang, Yuetao
Direct synthesis of sila-benzoazoles through hydrosilylation and rearrangement cascade reaction of benzoazoles and silanes
title Direct synthesis of sila-benzoazoles through hydrosilylation and rearrangement cascade reaction of benzoazoles and silanes
title_full Direct synthesis of sila-benzoazoles through hydrosilylation and rearrangement cascade reaction of benzoazoles and silanes
title_fullStr Direct synthesis of sila-benzoazoles through hydrosilylation and rearrangement cascade reaction of benzoazoles and silanes
title_full_unstemmed Direct synthesis of sila-benzoazoles through hydrosilylation and rearrangement cascade reaction of benzoazoles and silanes
title_short Direct synthesis of sila-benzoazoles through hydrosilylation and rearrangement cascade reaction of benzoazoles and silanes
title_sort direct synthesis of sila-benzoazoles through hydrosilylation and rearrangement cascade reaction of benzoazoles and silanes
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9911738/
https://www.ncbi.nlm.nih.gov/pubmed/36759604
http://dx.doi.org/10.1038/s41467-023-36360-z
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