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Rhodium hydride enabled enantioselective intermolecular C–H silylation to access acyclic stereogenic Si–H

The tremendous success of stereogenic carbon compounds has never ceased to inspire researchers to explore the potentials of stereogenic silicon compounds. Intermolecular C–H silylation thus represents the most versatile and straightforward strategy to construct C–Si bonds, however, its enantioselect...

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Autores principales: An, Kun, Ma, Wenpeng, Liu, Li-Chuan, He, Tao, Guan, Guiyu, Zhang, Qing-Wei, He, Wei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8844420/
https://www.ncbi.nlm.nih.gov/pubmed/35165278
http://dx.doi.org/10.1038/s41467-022-28439-w
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author An, Kun
Ma, Wenpeng
Liu, Li-Chuan
He, Tao
Guan, Guiyu
Zhang, Qing-Wei
He, Wei
author_facet An, Kun
Ma, Wenpeng
Liu, Li-Chuan
He, Tao
Guan, Guiyu
Zhang, Qing-Wei
He, Wei
author_sort An, Kun
collection PubMed
description The tremendous success of stereogenic carbon compounds has never ceased to inspire researchers to explore the potentials of stereogenic silicon compounds. Intermolecular C–H silylation thus represents the most versatile and straightforward strategy to construct C–Si bonds, however, its enantioselective variant has been scarcely reported to date. Herein we report a protocol that allows for the enantioselective intermolecular C–H bond silylation, leading to the construction of a wide array of acyclic stereogenic Si–H compounds under simple and mild reaction conditions. Key to the success is (1) a substrate design that prevents the self-reaction of prochiral silane and (2) the employment of a more reactive rhodium hydride ([Rh]-H) catalyst as opposed to the commonly used rhodium chloride ([Rh]-Cl) catalyst. This work unveils opportunities in converting simple arenes into value-added stereogenic silicon compounds.
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spelling pubmed-88444202022-03-04 Rhodium hydride enabled enantioselective intermolecular C–H silylation to access acyclic stereogenic Si–H An, Kun Ma, Wenpeng Liu, Li-Chuan He, Tao Guan, Guiyu Zhang, Qing-Wei He, Wei Nat Commun Article The tremendous success of stereogenic carbon compounds has never ceased to inspire researchers to explore the potentials of stereogenic silicon compounds. Intermolecular C–H silylation thus represents the most versatile and straightforward strategy to construct C–Si bonds, however, its enantioselective variant has been scarcely reported to date. Herein we report a protocol that allows for the enantioselective intermolecular C–H bond silylation, leading to the construction of a wide array of acyclic stereogenic Si–H compounds under simple and mild reaction conditions. Key to the success is (1) a substrate design that prevents the self-reaction of prochiral silane and (2) the employment of a more reactive rhodium hydride ([Rh]-H) catalyst as opposed to the commonly used rhodium chloride ([Rh]-Cl) catalyst. This work unveils opportunities in converting simple arenes into value-added stereogenic silicon compounds. Nature Publishing Group UK 2022-02-14 /pmc/articles/PMC8844420/ /pubmed/35165278 http://dx.doi.org/10.1038/s41467-022-28439-w 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
An, Kun
Ma, Wenpeng
Liu, Li-Chuan
He, Tao
Guan, Guiyu
Zhang, Qing-Wei
He, Wei
Rhodium hydride enabled enantioselective intermolecular C–H silylation to access acyclic stereogenic Si–H
title Rhodium hydride enabled enantioselective intermolecular C–H silylation to access acyclic stereogenic Si–H
title_full Rhodium hydride enabled enantioselective intermolecular C–H silylation to access acyclic stereogenic Si–H
title_fullStr Rhodium hydride enabled enantioselective intermolecular C–H silylation to access acyclic stereogenic Si–H
title_full_unstemmed Rhodium hydride enabled enantioselective intermolecular C–H silylation to access acyclic stereogenic Si–H
title_short Rhodium hydride enabled enantioselective intermolecular C–H silylation to access acyclic stereogenic Si–H
title_sort rhodium hydride enabled enantioselective intermolecular c–h silylation to access acyclic stereogenic si–h
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8844420/
https://www.ncbi.nlm.nih.gov/pubmed/35165278
http://dx.doi.org/10.1038/s41467-022-28439-w
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