Lewis acid catalyzed intermolecular olefin hydroamination: Scope, limitation, and mechanism

Article abstract of DOI:10.1002/ejoc.200701080

Intermolecular olefin hydroamination was studied by various Lewis acids. The results of ZrCl₄, FeCl₃, BiCl₃, and AlCl₃ catalyzed reactions of norbornene with aromatic amines were compared, and BiCl₃ was found to be the most effective catalyst to give high yields for various amines, whereas ZrCl₄ could promote the reactions at relatively low temperatures. The FeCl₃ catalyzed reactions were the most chemoselective and excellent yields could be achieved for certain amines by using AlCl₃. A carbocation mechanism was proposed, and the controllable syntheses of allylamine and tetrahydroquinoline from isoprene and 2,5-dichloroaniline were achieved by application of this mechanism. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.