4.8 Article

Intramolecular Benzyne-Phenolate [4+2] Cycloadditions

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 30, Pages 12440-12444

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202003131

Keywords

cycloaddition; benzyne; polycycles; silicon; synthetic methods

Funding

  1. Japan Society for the Promotion of Science (JSPS) [JP16H06351, JP18K06548]

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An intramolecular benzyne-phenolate [4+2] cycloaddition is reported. Benzyne precursors, having vicinal halogen-sulfonate functionalities, linked with a phenol(ate) by various tether groups undergo efficient intramolecular [4+2] cycloaddition by treatment with either Ph3MgLi or nBuLi for halogen-metal exchange to form various benzobarrelenes.

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