2-Bromo-6-(chlorodiisopropylsilyl)phenyl tosylate as an efficient platform for intramolecular benzyne–diene [4 + 2] cycloaddition

An intramolecular benzyne–diene [4 + 2] cycloaddition with broad substrate scope has been realized by using a cleavable silicon tether, allowing access to various polycyclic structures. 2-Bromo-6-(chlorodiisopropylsilyl)phenyl tosylate serves as an efficient platform for (1) rapid attachment of vari...

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Detalles Bibliográficos
Autores principales: Nishii, Arata, Takikawa, Hiroshi, Suzuki, Keisuke
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6461022/
https://www.ncbi.nlm.nih.gov/pubmed/31015926
http://dx.doi.org/10.1039/c8sc05518a
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author Nishii, Arata
Takikawa, Hiroshi
Suzuki, Keisuke
author_facet Nishii, Arata
Takikawa, Hiroshi
Suzuki, Keisuke
author_sort Nishii, Arata
collection PubMed
description An intramolecular benzyne–diene [4 + 2] cycloaddition with broad substrate scope has been realized by using a cleavable silicon tether, allowing access to various polycyclic structures. 2-Bromo-6-(chlorodiisopropylsilyl)phenyl tosylate serves as an efficient platform for (1) rapid attachment of various arynophiles to the benzyne precursor via a Si–O bond and (2) facile generation of benzyne via halogen–metal exchange with Ph(3)MgLi.
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spelling pubmed-64610222019-04-23 2-Bromo-6-(chlorodiisopropylsilyl)phenyl tosylate as an efficient platform for intramolecular benzyne–diene [4 + 2] cycloaddition Nishii, Arata Takikawa, Hiroshi Suzuki, Keisuke Chem Sci Chemistry An intramolecular benzyne–diene [4 + 2] cycloaddition with broad substrate scope has been realized by using a cleavable silicon tether, allowing access to various polycyclic structures. 2-Bromo-6-(chlorodiisopropylsilyl)phenyl tosylate serves as an efficient platform for (1) rapid attachment of various arynophiles to the benzyne precursor via a Si–O bond and (2) facile generation of benzyne via halogen–metal exchange with Ph(3)MgLi. Royal Society of Chemistry 2019-03-06 /pmc/articles/PMC6461022/ /pubmed/31015926 http://dx.doi.org/10.1039/c8sc05518a Text en This journal is © The Royal Society of Chemistry 2019 http://creativecommons.org/licenses/by-nc/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0)
spellingShingle Chemistry
Nishii, Arata
Takikawa, Hiroshi
Suzuki, Keisuke
2-Bromo-6-(chlorodiisopropylsilyl)phenyl tosylate as an efficient platform for intramolecular benzyne–diene [4 + 2] cycloaddition
title 2-Bromo-6-(chlorodiisopropylsilyl)phenyl tosylate as an efficient platform for intramolecular benzyne–diene [4 + 2] cycloaddition
title_full 2-Bromo-6-(chlorodiisopropylsilyl)phenyl tosylate as an efficient platform for intramolecular benzyne–diene [4 + 2] cycloaddition
title_fullStr 2-Bromo-6-(chlorodiisopropylsilyl)phenyl tosylate as an efficient platform for intramolecular benzyne–diene [4 + 2] cycloaddition
title_full_unstemmed 2-Bromo-6-(chlorodiisopropylsilyl)phenyl tosylate as an efficient platform for intramolecular benzyne–diene [4 + 2] cycloaddition
title_short 2-Bromo-6-(chlorodiisopropylsilyl)phenyl tosylate as an efficient platform for intramolecular benzyne–diene [4 + 2] cycloaddition
title_sort 2-bromo-6-(chlorodiisopropylsilyl)phenyl tosylate as an efficient platform for intramolecular benzyne–diene [4 + 2] cycloaddition
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6461022/
https://www.ncbi.nlm.nih.gov/pubmed/31015926
http://dx.doi.org/10.1039/c8sc05518a
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AT takikawahiroshi 2bromo6chlorodiisopropylsilylphenyltosylateasanefficientplatformforintramolecularbenzynediene42cycloaddition
AT suzukikeisuke 2bromo6chlorodiisopropylsilylphenyltosylateasanefficientplatformforintramolecularbenzynediene42cycloaddition

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