4.8 Article

Direct Assembly of 3,4-Difunctionalized Benzofurans and Polycyclic Benzofurans by Phenol Dearomatization and Palladium-Catalyzed Domino Reaction

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 26, Pages 6805-6809

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201404155

Keywords

benzofurans; dearomatization; domino reactions; multicomponent reactions; phenols

Funding

  1. National Science Foundation of China [21332009, 21102019]
  2. Shanghai Science and Technology Committee [13431900103]

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A method to directly convert 2-alkynylphenols to 3,4-difunctionalized benzofurans and polycyclic benzofurans was developed. This protocol involves a hypervalent-iodine-mediated oxidative dearomatization to break the aromaticity of 2-alkynylphenols, and a palladium-catalyzed domino reaction to install two functional groups at the C3 and the C4 positions and restore the aromaticity of benzofurans.

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