Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 354, Issue 1, Pages 159-170Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201100614
Keywords
copper; domino reactions; homogeneous catalysis; palladium
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Funding
- Ministero dell'Universita e della Ricerca [2008 KRBX3B]
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Intramolecular oxidative palladium-catalyzed reactions of indolylallylamides in the presence of the couple bis(acetonitrile) palladium dichloride and copper(II) halide are described. Starting from 2- and 3-indolylallylamides and involving in both cases the C-3 position of the indole nucleus, variously substituted beta-carbolinones were obtained by arylation/halogenation, arylation/esterification or arylation/carboalkoxylation processes. On the other hand, an unusual aminohalogenation/halogenation sequence performed on 2-indolylallylamides gave rise to pyrazino[1,2-a]indole products. The carboesterification process is the result of an unknown path that involves the DMF or DMA used as solvent. The outcome of the reactions of the 3-indolylallylamides arises from a totally selective 1,2-migration of the acyl group on the supposed spiro intermediates formed from the nucleophilic attack of the C-3 indole position.
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