Anti-Markovnikov functionalizations of unsaturated compounds, Part 7 - Amination of aromatic olefins with anilines: A new domino synthesis of quinolines

A new catalytic amination of aromatic olefins with anilines is presented. In a domino reaction, substituted quinoline derivatives are obtained in the presence of cationic rhodium complexes, such as [Rh(cod)(2)]BF4, and PPh3. Ethylbenzene is formed as a by-product in this new oxidative reaction. The...

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Published inChemistry : a European journal Vol. 6; no. 14; pp. 2513 - 2522
Main Authors Beller, M, Thiel, OR, Trauthwein, H, Hartung, CG
Format Journal Article
LanguageEnglish
Published BERLIN Wiley 17.07.2000
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
DIELS-ALDER REACTIONS
<4+2>CYCLOADDITION REACTION
ORGANOLANTHANIDE-CATALYZED HYDROAMINATION
BOND FORMATION
anti-Markovnikov aminations
UNPROTECTED AMINO OLEFINS
CHIRAL ORGANOLANTHANIDES
CATIONIC RHODIUM(I) COMPLEXES
TETRAHYDROQUINOLINE DERIVATIVES
homogeneous catalysis
domino reactions
NITROGEN DONORS
REGIOSPECIFIC CYCLIZATION
quinolines
rhodium
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Summary:A new catalytic amination of aromatic olefins with anilines is presented. In a domino reaction, substituted quinoline derivatives are obtained in the presence of cationic rhodium complexes, such as [Rh(cod)(2)]BF4, and PPh3. Ethylbenzene is formed as a by-product in this new oxidative reaction. The first transition metal catalyzed anti-Markovnikov hydroamination of styrene with anilines occurs as a side reaction. Mechanistic investigations strongly support the regioselective oxidative amination of styrene as the key reaction step.
ISSN:0947-6539
DOI:10.1002/1521-3765(20000717)6:14<2513::AID-CHEM2513>3.0.CO;2-V