Synthesis
DOI: 10.1055/s-0036-1590860
paper
© Georg Thieme Verlag Stuttgart · New York

The Palladium-Catalyzed Heteroarylation of Adamantylalkyl Amines with Dihalogenopyridines: Scope and Limitations

Anton S. Abela, Alexei D. Averina, b, Alexei K. Buryakb, Evgenii N. Savelyevc, Boris S. Orlinsonc, Ivan A. Novakovc, Irina P. Beletskaya*a, b
  • aDepartment of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1–3, Moscow 119991, Russian Federation
  • bA. N. Frumkin Institute of Physical Chemistry and Electrochemistry RAS, 31-4 Leninskii pr., Moscow 119991, Russian Federation
  • cVolgograd State Technical University, 28 pr. Lenina, Volgograd 400005, Russian Federation   Email: alexaveron@yandex.ru
This work was financially supported by the Russian Foundation for Basic Research grants 13-03-00572 and 16-03-00349.
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Publication History

Received: 15 June 2017

Accepted after revision: 12 July 2017

Publication Date:
07 August 2017 (eFirst)

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.

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