Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 11, Issue 21, Pages 3090-3096Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201601067
Keywords
cyclocarbonylation; indolones; palladium; regioselectivity; synthetic methods
Categories
Funding
- National Natural Science Foundation of China [21202040, 21572047]
- China Postdoctoral Science Foundation [2014M552007, 2015T80771]
- Program for Innovative Research Team in Science and Technology in University of Henan Province [15IRTSTHN003]
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A highly efficient and regioselective synthetic route to 6H-isoindolo[2,1-a]indol-6-ones and indeno[1,2-b]indol-10(5H)-ones through the Pd-catalyzed cyclocarbonylation of 2-(2-bromoaryl)indoles under atmospheric CO pressure has been achieved. Notably, the regioselectivity of the reaction was exclusively dependent on the structural characteristics of the indole substrates. With N-unsubstituted indoles as the starting materials, the reaction afforded 6H-isoindolo[2,1-a]indol-6-ones in good-to-excellent yields. On the other hand, with N-substituted indoles as the substrates, the reaction gave indeno[1,2-b]indol-10(5H)-ones in a highly regioselective manner.
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