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

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 i...

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Bibliographic Details
Published inChemistry : a European journal Vol. 21; no. 11; pp. 4242 - 4246
Main Authors Fu, Xu-Fei, Xiang, Yu, Yu, Zhi-Xiang
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 09.03.2015
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
ACTIVATION
INSERTION
RING-EXPANSION
CARBOCYCLIZATION
benzo/[7+1]
ALKYNES
ENE-VINYLCYCLOPROPANES
ORIGINS
benzocyclobutene
OLEFINS
ELECTROCYCLIC REACTIONS
carbonylation
INTRAMOLECULAR 5+2 CYCLOADDITIONS
eight-membered ring
rhodium
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Summary: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.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201405712