Arylation of Adamantanamines: X. Palladium- and Copper-Catalyzed Heteroarylation of Adamantane-Containing Amines with Bromopyridines
M S Lyakhovich
1
,
A V Murashkina
1
,
A D Averin
1, 2
,
A S Abel
1
,
O A Maloshitskaya
1
,
E N Savelyev
3
,
B S Orlinson
3
,
I P Beletskaya
1, 2
Publication type: Journal Article
Publication date: 2019-06-01
scimago Q4
wos Q4
SJR: 0.190
CiteScore: 1.3
Impact factor: 0.9
ISSN: 10704280, 16083393
Organic Chemistry
Abstract
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.
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Lyakhovich M. S. et al. Arylation of Adamantanamines: X. Palladium- and Copper-Catalyzed Heteroarylation of Adamantane-Containing Amines with Bromopyridines // Russian Journal of Organic Chemistry. 2019. Vol. 55. No. 6. pp. 737-747.
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Lyakhovich M. S., Murashkina A. V., Averin A. D., Abel A. S., Maloshitskaya O. A., Savelyev E. N., Orlinson B. S., Beletskaya I. P. Arylation of Adamantanamines: X. Palladium- and Copper-Catalyzed Heteroarylation of Adamantane-Containing Amines with Bromopyridines // Russian Journal of Organic Chemistry. 2019. Vol. 55. No. 6. pp. 737-747.
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RIS
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TY - JOUR
DO - 10.1134/S1070428019060010
UR - https://doi.org/10.1134/S1070428019060010
TI - Arylation of Adamantanamines: X. Palladium- and Copper-Catalyzed Heteroarylation of Adamantane-Containing Amines with Bromopyridines
T2 - Russian Journal of Organic Chemistry
AU - Lyakhovich, M S
AU - Murashkina, A V
AU - Averin, A D
AU - Abel, A S
AU - Maloshitskaya, O A
AU - Savelyev, E N
AU - Orlinson, B S
AU - Beletskaya, I P
PY - 2019
DA - 2019/06/01
PB - Pleiades Publishing
SP - 737-747
IS - 6
VL - 55
SN - 1070-4280
SN - 1608-3393
ER -
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@article{2019_Lyakhovich,
author = {M S Lyakhovich and A V Murashkina and A D Averin and A S Abel and O A Maloshitskaya and E N Savelyev and B S Orlinson and I P Beletskaya},
title = {Arylation of Adamantanamines: X. Palladium- and Copper-Catalyzed Heteroarylation of Adamantane-Containing Amines with Bromopyridines},
journal = {Russian Journal of Organic Chemistry},
year = {2019},
volume = {55},
publisher = {Pleiades Publishing},
month = {jun},
url = {https://doi.org/10.1134/S1070428019060010},
number = {6},
pages = {737--747},
doi = {10.1134/S1070428019060010}
}
Cite this
MLA
Copy
Lyakhovich, M. S., et al. “Arylation of Adamantanamines: X. Palladium- and Copper-Catalyzed Heteroarylation of Adamantane-Containing Amines with Bromopyridines.” Russian Journal of Organic Chemistry, vol. 55, no. 6, Jun. 2019, pp. 737-747. https://doi.org/10.1134/S1070428019060010.
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