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

• 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
• ISSN: 1066-5285; 1573-9171
• DOI: 10.1007/s11172-021-3328-7

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.