Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 35, Pages 12303-12307Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201502327
Keywords
carbopalladation; domino reaction; heterocycles; Heck reaction; palladium
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Funding
- German Research Foundation (DFG) [WE2932/7-1]
- Fonds der Chemischen Industrie
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An intramolecular domino process consisting of a formal anti-carbopalladation followed by Heck reaction is realized. Complex oligo(hetero)cyclic scaffolds are efficiently obtained in one synthetic step from easily obtainable enyne precursors. In contrast to common syn-carbopalladation reactions of alkyne units, the carbopalladation employed here is designed to afford an anti-arrangement of the two new substituents across the emerging double bond. A prerequisite is that the residues next to the alkyne should lack any beta-hydrogen atoms. The method paves the way to tri- and tetrasubstituted double-bond systems that have not been accessible by conventional Pd catalysis.
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