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Palladium-Catalyzed Amination of Dichloroquinolines with Adamantane-Containing Amines
Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory, 1-3, Moscow 119991, Russia
Volgograd State Technical University, 28 Lenina prosp., Volgograd 400131, Russia
* Author to whom correspondence should be addressed.
Received: 31 December 2012; in revised form: 24 January 2013 / Accepted: 1 February 2013 / Published: 6 February 2013
Abstract: Pd-catalyzed amination of isomeric 2,6-, 2,8-, 4,8- and 4,7-dichloroquinolines was studied using adamantane-containing amines in which substituents at the nitrogen atom differ in bulkiness. The selectivity of the amination of 2,6-dichloroquinoline was very low, substantially better results were obtained with 2,8-dichloroquinoline, and 4,8- and 4,7-dichloroquinolines provided the best yields of the amination products. Diamination of 4,8- and 4,7-dichloroquinolines was carried out with two amines which differ strongly in the bulkiness of the alkyl group. In the majority of cases BINAP ligand was successfully applied, however, it had to be replaced with DavePhos in certain reactions when using the most sterically hindered amine as well as for the diamination reactions.
Keywords: amines; adamantane; Pd catalysis; amination; quinoline
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Abel, A.S.; Averin, A.D.; Maloshitskaya, O.A.; Savelyev, E.N.; Orlinson, B.S.; Novakov, I.A.; Beletskaya, I.P. Palladium-Catalyzed Amination of Dichloroquinolines with Adamantane-Containing Amines. Molecules 2013, 18, 2096-2109.
Abel AS, Averin AD, Maloshitskaya OA, Savelyev EN, Orlinson BS, Novakov IA, Beletskaya IP. Palladium-Catalyzed Amination of Dichloroquinolines with Adamantane-Containing Amines. Molecules. 2013; 18(2):2096-2109.
Abel, Anton S.; Averin, Alexei D.; Maloshitskaya, Olga A.; Savelyev, Evgenii N.; Orlinson, Boris S.; Novakov, Ivan A.; Beletskaya, Irina P. 2013. "Palladium-Catalyzed Amination of Dichloroquinolines with Adamantane-Containing Amines." Molecules 18, no. 2: 2096-2109.