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
Descripción
Sumario: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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