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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...

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Autores principales: Takeda, Youhei, Shibuta, Kaoru, Aoki, Shohei, Tohnai, Norimitsu, Minakata, Satoshi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2019
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.
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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
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
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
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
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
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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