Palladium-Catalyzed Amination of Dichloroquinolines with Adamantane-Containing Amines

Molecules

Anton S. Abel¹  Alexei D. Averin¹  Olga A. Maloshitskaya¹  Evgenii N. Savelyev¹  Boris S. Orlinson¹  Ivan A. Novakov¹ 

[1]¹Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory, 1-3, Moscow 119991, Russia[2] height:6px

[3]"> ²Volgograd State Technical University, 28 Lenina prosp., Volgograd 400131, Russia

关键词: amines;    adamantane;    Pd catalysis;    amination;    quinoline;   

DOI  :  10.3390/molecules18022096

来源: mdpi

【 摘 要 】

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- and4,7-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.

【 授权许可】

CC BY   
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.