Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 46, Pages 14405-14408Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201608247
Keywords
bisallene; carbocyclization; olefins; palladium; seven-membered carbocycles
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Funding
- European Research Council [ERC AdG 247014]
- Swedish Research Council [621-2013-4653]
- Berzelii Center EXSELENT
- Knut and Alice Wallenberg Foundation
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An olefin-assisted palladium-catalyzed oxidative carbocyclization-alkoxycarbonylation of bisallenes to afford seven-membered carbocycles has been established. This dehydrogenative coupling reaction showed excellent substrate scope and functional group compatibility. The reaction exhibited high chemo-and regioselectivity, and ester 3 was the only product obtained. The olefin unit has been proven to be indispensable during the reaction. Moreover, intramolecular oxidative coupling suggests that the reaction proceeds via a (pallyl)palladium intermediate.
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