Arylation of Adamantanamines: X. Palladium- and Copper-Catalyzed Heteroarylation of Adamantane-Containing Amines with Bromopyridines


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Resumo

The catalytic efficiencies of palladium(0) and copper(I) complexes in the amination of 2-bromopyridine and its fluorine-containing derivatives with (1-adamantyl)methanamine and 2-(1-adamantyloxy)ethanamine were compared. Both types of catalytic systems were shown to be applicable for the preparation of the corresponding N-pyridyl derivatives from 3- and 5-fluoro- and 4-, 5-, and 6-trifluoromethyl-2-bromopyridines. DavePhos was found to be the most efficient ligand in the Pd(0)-catalyzed reactions; however, the reactions with 2-bromo-4-(trifluoromethyl)pyridine and 2-bromo-5-(trifluoromethyl)pyridine were accompanied by formation of a considerable amount of the diarylation product. The diarylation process was significantly suppressed in the presence of copper(I) complexes.

Sobre autores

O. Maloshitskaya

Faculty of Chemistry

Email: averin@org.chem.msu.ru
Rússia, Moscow

E. Savelyev

Volgograd State Technical University

Email: averin@org.chem.msu.ru
Rússia, Volgograd

B. Orlinson

Volgograd State Technical University

Email: averin@org.chem.msu.ru
Rússia, Volgograd

I. Beletskaya

Faculty of Chemistry; Frumkin Institute of Physical Chemistry and Electrochemistry

Email: averin@org.chem.msu.ru
Rússia, Moscow; Moscow

M. Lyakhovich

Faculty of Chemistry

Email: averin@org.chem.msu.ru
Rússia, Moscow

A. Murashkina

Faculty of Chemistry

Email: averin@org.chem.msu.ru
Rússia, Moscow

A. Averin

Faculty of Chemistry; Frumkin Institute of Physical Chemistry and Electrochemistry

Autor responsável pela correspondência
Email: averin@org.chem.msu.ru
Rússia, Moscow; Moscow

A. Abel

Faculty of Chemistry

Email: averin@org.chem.msu.ru
Rússia, Moscow

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