2,7-Dibromonaphthalene and 4,4′-dibromobiphenyl in the synthesis of oxadiamine N, N, N′, N′-tetraaryl derivatives and studies of formation of bismacrocyclic compounds from them

The Pd-catalyzed tetraarylation of diamines and oxadiamines with 2,7-dibromonaphthalenes and 4,4′-dibromobiphenyl was studied. These reactions gave the corresponding N,N,N ′, N ′-tetra(bromoaryl) derivatives in the yields up to 50%. The product yields strongly depend on the structure of the starting...

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Bibliographic Details
Published in:Russian chemical bulletin 2021-11, Vol.70 (11), p.2164-2179
Main Authors: Averin, A. D., Uglov, A. N., Zubrienko, G. A., Abel, A. S., Buryak, A. K., Beletskaya, I. P.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Diamines
Full Articles
Inorganic Chemistry
Isomers
Naphthalene
Organic Chemistry
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Summary:The Pd-catalyzed tetraarylation of diamines and oxadiamines with 2,7-dibromonaphthalenes and 4,4′-dibromobiphenyl was studied. These reactions gave the corresponding N,N,N ′, N ′-tetra(bromoaryl) derivatives in the yields up to 50%. The product yields strongly depend on the structure of the starting diamines. The synthesized compounds were involved in the Pd-catalyzed amination with 2 equiv. of oxadiamines to give bismacrocyclic compounds. It was demonstrated that naphthyl derivatives generally produced the mixtures of structural isomers, i.e. , bismacrocycles and macrobicycles (cryptands). The better yields of macrocyclization were achieved with naphthalene diamine derivatives and the net results of macrocyclization are predetermined by the structure of the oxadiamine moieties in both reacting molecules.
ISSN:1066-5285
1573-9171
DOI:10.1007/s11172-021-3328-7