Cationic organoaluminum compounds as intramolecular hydroamination catalysts |
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| Institution: | 1. Department of Laser Science and Interaction, National Institute of Laser Enhanced Science, Cairo University, 12613 Giza, Egypt;2. Department of Laser Applications in Metrology, Photochemistry & Agriculture, National Institute of Laser Enhanced Science, Cairo University, 12613 Giza, Egypt;1. University of Paris-Descartes, Faculty of Pharmacy, Laboratory of Physical Chemistry, 4 avenue de l’Observatoire, 75006 Paris, France;2. University of Paris-Sud, Faculty of Pharmacy, Groupe Matériaux et Santé EA 401, 5 rue Jean-Baptiste Clément, 92296 Châtenay-Malabry, France;3. Assistance Publique-Hôpitaux de Paris, Agence Générale des Equipements et Produits de Santé, Département de Contrôle Qualité et Développement Analytique, 7 rue du Fer à Moulin, 75005 Paris, France;4. Solvay SA, 25 rue de Clichy, 75009 Paris, France;5. 78170 La Celle St Cloud, France;6. University of Monastir, Faculty of Pharmacy, Laboratory of Analytical Chemistry, rue Ibn Sian, 5000 Monastir, Tunisia;1. Applied Science College, Harbin University of Science and Technology, Harbin 150080, PR China;2. Department of the applied chemistry, Harbin Institute of Technology, Harbin 150001, PR China;3. Computer science and technology, Harbin University of Science and Technology, Harbin 150080, PR China |
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| Abstract: | Cationic dialkylaluminum and m-terphenylalkylaluminum compounds catalyze the intramolecular hydroamination of primary and secondary aminopentenes. The reaction rates are strongly dependent on the substrate and the catalyst substituents. The bulky species Dipp1AlEt]CHB11H5I6] (Dipp1 = 2,6-Dipp2C6H3–, Dipp = 2,6-iPr2C6H3–), 4, was the most active catalyst. Although the neutral species DcpAlEt2 (Dcp = 2,6-(2,6-Cl2C6H3)2C6H3–), 7, and Dipp1AlEt2, 8, showed some catalytic activity, they were more than 25 times less reactive than their cationic counterparts DcpAlEt]CHB11H5Cl6], 3, and 4. The cyclization of secondary benzylaminopentenes with Et2Al]CHB11H5I6], 1, was strongly dependent on the substitution of the C-2 olefinic carbon. |
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