Premium
Copper(I)‐Catalyzed Amination of Halogenopyridines with Polyamines
Author(s) -
Anokhin Maksim V.,
Averin Alexei D.,
Panchenko Svetlana P.,
Maloshitskaya Olga A.,
Buryak Alexei K.,
Beletskaya Irina P.
Publication year - 2015
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201400092
Subject(s) - chemistry , amination , diamine , catalysis , polyamine , ligand (biochemistry) , combinatorial chemistry , medicinal chemistry , copper , propane , organic chemistry , stereochemistry , receptor , biochemistry
Cu I ‐Catalyzed amination of 2‐bromo‐, and 2‐, 3‐, and 4‐iodopyridines with tri‐ and tetraamines aimed at the synthesis of N , N′ ‐diheteroaryl derivatives was studied. A strong dependence of the product yields on the nature of starting compounds and the ligand used was observed. The increase in the number of ethene‐1,2‐diamine fragments in the polyamine structure led to the increase in the yields of polyheteroarylated compounds, whereas propane‐1,3‐diamine fragments favored the formation of monopyridinyl derivatives and promoted the heteroarylation of the secondary amino groups. 2‐Iodopyridine, as a more reactive compound, readily formed N , N ‐diarylated products. The best yields of the target N , N′ ‐dipyridin‐2‐yl derivatives were 76% in the case of the triamine and 68% in the case of the tetraamine. A comparison of Cu I ‐ and Pd 0 ‐mediated heteroarylation of polyamines was also presented.