Abstract
Palladium-catalyzed heteroarylation of adamantylalkyl amines characterized by different
steric hindrances at the amino group was carried out using 2,3-, 2,5-, 2,6-, and 3,5-dihalogenopyridines.
The dependence of the results of the coupling on the nature of the halogen atoms (bromine,
chlorine), their position in the pyridine ring, and on the structure of adamantylalkyl
amines was investigated. The application of dichloropyridines or bromochloropyridines
was shown to be advantageous over the use dibromopyridines in many cases. Selective
substitution of bromine atom in positions 3 and 5 in the presence of chlorine atom
in position 2 of the pyridine ring was observed. The possibility of N,N-diheteroarylation of adamantane-containing amines with 2,5-dihalogenopyridines was
shown, and diamination of 2,6- and 3,5-dihalogenopyridines was demonstrated.
Key words
palladium catalysis - amination - halogenopyridines - adamantane - amines
