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Molecules 2013, 18(2), 2096-2109; doi:10.3390/molecules18022096
Article

Palladium-Catalyzed Amination of Dichloroquinolines with Adamantane-Containing Amines

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Received: 31 December 2012 / Revised: 24 January 2013 / Accepted: 1 February 2013 / Published: 6 February 2013
(This article belongs to the Special Issue Advances in Heteroaromatic Chemistry)
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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 amines; adamantane; Pd catalysis; amination; quinoline
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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.

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