Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 16, Issue 42, Pages 12746-12753Publisher
WILEY-BLACKWELL
DOI: 10.1002/chem.201001535
Keywords
cyclization; Heck reaction; heterocycles; homogeneous catalysis; palladium
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Funding
- Spanish Ministerio de Educacion y Ciencia [CTQ2008-06647, CTQ2009-14186]
- Xunta de Galicia (IN-BIOMED)
- Universidad del Pais Vasco
- Universidade de Vigo
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Structurally diverse C3-alkenylbenzofurans, C3-alkenylindoles, and C4-alkenylisoquinolones are efficiently prepared by using consecutive Sonogashira and cascade Pd-catalyzed heterocyclization/oxidative Heck couplings from readily available ortho-iodosubstituted phenol, aniline, and benzamide substrates, alkynes, and functionalized olefins. The cyclization of O- and N-heteronucleophiles follows regioselec-tive 5-endo-dig- or 6-endo-dig-cyclization modes, whereas the subsequent Heck-type coupling with both mono- and disubstituted olefins takes place stereoselectively with exclusive formation of the E isomers in most cases.
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