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Facile preparation of organosilanes from benzylboronates and gem-diborylalkanes mediated by KO(t)Bu

Methods to efficiently synthesize organosilanes are valuable in the fields of synthetic chemistry and materials science. During the past decades, boron conversion has become a generic and powerful approach for constructing carbon–carbon and other carbon–heteroatom bonds, but its potential applicatio...

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Detalles Bibliográficos
Autores principales: Tang, Man, Zhu, Wenyan, Sun, Huaxing, Wang, Jing, Jing, Su, Wang, Minyan, Shi, Zhuangzhi, Hu, Jiefeng
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/PMC10321478/
https://www.ncbi.nlm.nih.gov/pubmed/37416710
http://dx.doi.org/10.1039/d3sc02461j
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author Tang, Man
Zhu, Wenyan
Sun, Huaxing
Wang, Jing
Jing, Su
Wang, Minyan
Shi, Zhuangzhi
Hu, Jiefeng
author_facet Tang, Man
Zhu, Wenyan
Sun, Huaxing
Wang, Jing
Jing, Su
Wang, Minyan
Shi, Zhuangzhi
Hu, Jiefeng
author_sort Tang, Man
collection PubMed
description Methods to efficiently synthesize organosilanes are valuable in the fields of synthetic chemistry and materials science. During the past decades, boron conversion has become a generic and powerful approach for constructing carbon–carbon and other carbon–heteroatom bonds, but its potential application in forming carbon–silicon remains unexplored. Herein, we describe an alkoxide base-promoted deborylative silylation of benzylic organoboronates, geminal bis(boronates) or alkyltriboronates, allowing for straightforward access to synthetically valuable organosilanes. This selective deborylative methodology exhibits operational simplicity, broad substrate scope, excellent functional group compatibility and convenient scalability, providing an effective and complementary platform for the generation of diversified benzyl silanes and silylboronates. Detailed experimental results and calculated studies revealed an unusual mechanistic feature of this C–Si bond formation.
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spelling pubmed-103214782023-07-06 Facile preparation of organosilanes from benzylboronates and gem-diborylalkanes mediated by KO(t)Bu Tang, Man Zhu, Wenyan Sun, Huaxing Wang, Jing Jing, Su Wang, Minyan Shi, Zhuangzhi Hu, Jiefeng Chem Sci Chemistry Methods to efficiently synthesize organosilanes are valuable in the fields of synthetic chemistry and materials science. During the past decades, boron conversion has become a generic and powerful approach for constructing carbon–carbon and other carbon–heteroatom bonds, but its potential application in forming carbon–silicon remains unexplored. Herein, we describe an alkoxide base-promoted deborylative silylation of benzylic organoboronates, geminal bis(boronates) or alkyltriboronates, allowing for straightforward access to synthetically valuable organosilanes. This selective deborylative methodology exhibits operational simplicity, broad substrate scope, excellent functional group compatibility and convenient scalability, providing an effective and complementary platform for the generation of diversified benzyl silanes and silylboronates. Detailed experimental results and calculated studies revealed an unusual mechanistic feature of this C–Si bond formation. The Royal Society of Chemistry 2023-06-13 /pmc/articles/PMC10321478/ /pubmed/37416710 http://dx.doi.org/10.1039/d3sc02461j Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Tang, Man
Zhu, Wenyan
Sun, Huaxing
Wang, Jing
Jing, Su
Wang, Minyan
Shi, Zhuangzhi
Hu, Jiefeng
Facile preparation of organosilanes from benzylboronates and gem-diborylalkanes mediated by KO(t)Bu
title Facile preparation of organosilanes from benzylboronates and gem-diborylalkanes mediated by KO(t)Bu
title_full Facile preparation of organosilanes from benzylboronates and gem-diborylalkanes mediated by KO(t)Bu
title_fullStr Facile preparation of organosilanes from benzylboronates and gem-diborylalkanes mediated by KO(t)Bu
title_full_unstemmed Facile preparation of organosilanes from benzylboronates and gem-diborylalkanes mediated by KO(t)Bu
title_short Facile preparation of organosilanes from benzylboronates and gem-diborylalkanes mediated by KO(t)Bu
title_sort facile preparation of organosilanes from benzylboronates and gem-diborylalkanes mediated by ko(t)bu
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10321478/
https://www.ncbi.nlm.nih.gov/pubmed/37416710
http://dx.doi.org/10.1039/d3sc02461j
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