title: Palladium-catalyzed amination of dichloroquinolines with adamantane-containing amines.
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.
authors: Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1-3, Moscow 119991, Russia.
authors: Anton S
authors: AS
authors: Abel
authors: Alexei D
authors: AD
authors: Averin
authors: Olga A
authors: OA
authors: Maloshitskaya
authors: Evgenii N
authors: EN
authors: Savelyev
authors: Boris S
authors: BS
authors: Orlinson
authors: Ivan A
authors: IA
authors: Novakov
authors: Irina P
authors: IP
authors: Beletskaya
mesh_terms: D000218:Adamantane / Q000737:chemistry*; D000586:Amination; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D010165:Palladium / Q000737:chemistry*; D011804:Quinolines / Q000737:chemistry*
chemical_list: D000588:Amines; D011804:Quinolines; D010165:Palladium; D000218:Adamantane
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