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A General Synthesis of Alkenyl‐Substituted Benzofurans, Indoles, and Isoquinolones by Cascade Palladium‐Catalyzed Heterocyclization/Oxidative Heck Coupling
Author(s) -
Álvarez Rosana,
Martínez Claudio,
Madich Youssef,
Denis J. Gabriel,
Aurrecoechea José M.,
de Lera Ángel R.
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201001535
Subject(s) - chemistry , regioselectivity , aniline , sonogashira coupling , palladium , heck reaction , benzamide , oxidative phosphorylation , catalysis , organic chemistry , cascade , phenol , medicinal chemistry , combinatorial chemistry , biochemistry , chromatography
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 regioselective 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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