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

被引：9
作者：
Lyakhovich, M. S. [1 ]
Murashkina, A. V. [1 ]
Averin, A. D. [1 ,2 ]
Abel, A. S. [1 ]
Maloshitskaya, O. A. [1 ]
Savelyev, E. N. [3 ]
Orlinson, B. S. [3 ]
Beletskaya, I. P. [1 ,2 ]
机构：
[1] Moscow MV Lomonosov State Univ, Fac Chem, Moscow, Russia
[2] Frumkin Inst Phys Chem & Electrochem, Moscow, Russia
[3] Volgograd State Tech Univ, Volgograd, Russia
来源：
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 55卷 / 06期
基金：
俄罗斯基础研究基金会;
关键词：
adamantane; amines; pyridine; amination; homogeneous catalysis; palladium and copper complexes; DISCOVERY; OPTIMIZATION; AMINATION; POTENT; DERIVATIVES; INHIBITORS; CHEMISTRY; FAMILY; SERIES;
D O I：
10.1134/S1070428019060010
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
引用
收藏
页码：737 / 747
页数：11
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