Synthesis of polyaza macrocycles by palladium-catalyzed amination of 1,2-dibromobenzene and 2-bromo-1,3-dichlorobenzene |
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Authors: | A D Averin A V Shukhaev A K Buryak I P Beletskaya |
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Institution: | 1.Faculty of Chemistry,Moscow State University,Moscow,Russia;2.Frumkin Institute of Physical Chemistry and Electrochemistry,Russian Academy of Sciences,Moscow,Russia |
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Abstract: | Palladium-catalyzed amination of 1,2-dibromobenzene with equimolar amounts of linear polyamines leads to the formation of
polyaza macrocycles in low yields. The use of 2-bromo-1,3-dichlorobenzene as starting compound ensures considerably larger
yields of the target macrocycles, and the reaction is accompanied by side formation of N-aryl- and N,N′-diaryl-substituted polyamines, as well as of cyclic oligomers. The yields strongly depend on the polyamine chain length.
Reactions of excess 2-bromo-1,3-dichlorobenzene with a series of polyamines gave the corresponding N,N′-diarylpolyamines in high yields, and the latter reacted with the second polyamine molecule to form cyclic dimers. A relation
between the yield of cyclic dimers and polyamine structure was revealed. |
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