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 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.
Beller
M
M
Institut für Organische Katalyseforschung, an der Universität Rostock e.V., Germany. matthias.beller@ifok.uni-rostock.de
Thiel
O R
OR
Trauthwein
H
H
Hartung
C G
CG
D000475:Alkenes / Q000737:chemistry / Q000378:metabolism*; D000586:Amination; D000588:Amines / Q000378:metabolism*; D000814:Aniline Compounds / Q000378:metabolism*; D000962:Antimalarials / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D001555:Benzene Derivatives / Q000378:metabolism; D002384:Catalysis; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D016877:Oxidants / Q000378:metabolism; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D012238:Rhodium / Q000378:metabolism; D013343:Styrenes / Q000378:metabolism
D000475:Alkenes; D000588:Amines; D000814:Aniline Compounds; D000962:Antimalarials; D001555:Benzene Derivatives; D016877:Oxidants; D011804:Quinolines; D013343:Styrenes; D012238:Rhodium; C004912:ethylbenzene; C023650:aniline