4.6 Article

RhI-Catalyzed Benzo/[7+1] Cycloaddition of Cyclopropyl-Benzocyclobutenes and CO by Merging Thermal and Metal-Catalyzed C-C Bond Cleavages

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 11, Pages 4242-4246

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201405712

Keywords

benzo/[7+1]; benzocyclobutene; carbonylation; eight-membered ring; rhodium

Funding

  1. Natural Science Foundation of China [21232001]
  2. National Basic Research Program of China-973 Program [2011CB808600]

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A Rh-catalyzed benzo/[7+1] cycloaddition of cyclopropyl-benzocyclobutenes (CP-BCBs) and CO to benzocyclooctenones has been developed. In this reaction, CPBCB acts as a benzo/7-C synthon and the reaction involves two C-C bond cleavages: a thermal electrocyclic ring-opening of the four-membered ring in CP-BCB and a Rh-catalyzed C-C cleavage of the cyclopropane ring.

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