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

ABSTRACT: 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 Ph₃MgLi.

SUBMITTER: Nishii A

PROVIDER: S-EPMC6461022 | biostudies-literature | 2019 Apr

REPOSITORIES: biostudies-literature

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

Nishii Arata A Takikawa Hiroshi H Suzuki Keisuke K

Chemical science 20190306 13

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 Ph3MgLi. ...[more]

PMID: 31015926

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