Amination of Aromatic Olefins with Anilines: A New Domino Synthesis of Quinolines
- 7 July 2000
- journal article
- research article
- Published by Wiley in Chemistry – A European Journal
- Vol. 6 (14) , 2513-2522
- https://doi.org/10.1002/1521-3765(20000717)6:14<2513::aid-chem2513>3.0.co;2-v
Abstract
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.Keywords
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