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Catalyst-controlled regiodivergent ring-opening C(sp(3))–Si bond-forming reactions of 2-arylaziridines with silylborane enabled by synergistic palladium/copper dual catalysis
A catalyst-controlled regiodivergent and stereospecific ring-opening C(sp(3))–Si cross-coupling of 2-arylaziridines with silylborane enabled by synergistic Pd/Cu dual catalysis has been developed. Just by selecting a suitable combination of catalysts, the regioselectivity of the coupling is complete...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Royal Society of Chemistry
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6844297/ https://www.ncbi.nlm.nih.gov/pubmed/31803438 http://dx.doi.org/10.1039/c9sc02507c |
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author | Takeda, Youhei Shibuta, Kaoru Aoki, Shohei Tohnai, Norimitsu Minakata, Satoshi |
author_facet | Takeda, Youhei Shibuta, Kaoru Aoki, Shohei Tohnai, Norimitsu Minakata, Satoshi |
author_sort | Takeda, Youhei |
collection | PubMed |
description | A catalyst-controlled regiodivergent and stereospecific ring-opening C(sp(3))–Si cross-coupling of 2-arylaziridines with silylborane enabled by synergistic Pd/Cu dual catalysis has been developed. Just by selecting a suitable combination of catalysts, the regioselectivity of the coupling is completely switched to efficiently provide two regioisomers of β-silylamines (i.e., β-silyl-α-phenethylamines and β-silyl-β-phenethylamines) in good to high yields. Furthermore, a slight modification of the reaction conditions caused a drastic change in reaction pathways, leading to a tandem reaction to produce another regioisomer of silylamine (i.e., α-silyl-β-phenethylamines) in an efficient and selective manner. |
format | Online Article Text |
id | pubmed-6844297 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-68442972019-12-04 Catalyst-controlled regiodivergent ring-opening C(sp(3))–Si bond-forming reactions of 2-arylaziridines with silylborane enabled by synergistic palladium/copper dual catalysis Takeda, Youhei Shibuta, Kaoru Aoki, Shohei Tohnai, Norimitsu Minakata, Satoshi Chem Sci Chemistry A catalyst-controlled regiodivergent and stereospecific ring-opening C(sp(3))–Si cross-coupling of 2-arylaziridines with silylborane enabled by synergistic Pd/Cu dual catalysis has been developed. Just by selecting a suitable combination of catalysts, the regioselectivity of the coupling is completely switched to efficiently provide two regioisomers of β-silylamines (i.e., β-silyl-α-phenethylamines and β-silyl-β-phenethylamines) in good to high yields. Furthermore, a slight modification of the reaction conditions caused a drastic change in reaction pathways, leading to a tandem reaction to produce another regioisomer of silylamine (i.e., α-silyl-β-phenethylamines) in an efficient and selective manner. Royal Society of Chemistry 2019-07-31 /pmc/articles/PMC6844297/ /pubmed/31803438 http://dx.doi.org/10.1039/c9sc02507c Text en This journal is © The Royal Society of Chemistry 2019 https://creativecommons.org/licenses/by/3.0/This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0) |
spellingShingle | Chemistry Takeda, Youhei Shibuta, Kaoru Aoki, Shohei Tohnai, Norimitsu Minakata, Satoshi Catalyst-controlled regiodivergent ring-opening C(sp(3))–Si bond-forming reactions of 2-arylaziridines with silylborane enabled by synergistic palladium/copper dual catalysis |
title | Catalyst-controlled regiodivergent ring-opening C(sp(3))–Si bond-forming reactions of 2-arylaziridines with silylborane enabled by synergistic palladium/copper dual catalysis
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title_full | Catalyst-controlled regiodivergent ring-opening C(sp(3))–Si bond-forming reactions of 2-arylaziridines with silylborane enabled by synergistic palladium/copper dual catalysis
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title_fullStr | Catalyst-controlled regiodivergent ring-opening C(sp(3))–Si bond-forming reactions of 2-arylaziridines with silylborane enabled by synergistic palladium/copper dual catalysis
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title_full_unstemmed | Catalyst-controlled regiodivergent ring-opening C(sp(3))–Si bond-forming reactions of 2-arylaziridines with silylborane enabled by synergistic palladium/copper dual catalysis
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title_short | Catalyst-controlled regiodivergent ring-opening C(sp(3))–Si bond-forming reactions of 2-arylaziridines with silylborane enabled by synergistic palladium/copper dual catalysis
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title_sort | catalyst-controlled regiodivergent ring-opening c(sp(3))–si bond-forming reactions of 2-arylaziridines with silylborane enabled by synergistic palladium/copper dual catalysis |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6844297/ https://www.ncbi.nlm.nih.gov/pubmed/31803438 http://dx.doi.org/10.1039/c9sc02507c |
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