Copper and Copper Oxide Nanoparticles in the Synthesis of N-Arylamines of the Adamantane Series

Murashkina, A.V.; Fomenko, V.I.; Averin, A.D.; Shesterkina, A.A.; Savelyev, E.N.; Novakov, I.A.; Beletskaya, I.P.

Авторы: Murashkina A.V., Fomenko V.I., Averin A.D., Shesterkina A.A., Savelyev E.N., Novakov I.A., Beletskaya I.P.
Журнал: Russian Journal of Organic Chemistry
Том: 61
Номер: 10
Год издания: 2025
Издательство: Maik Nauka/Interperiodica Publishing
Местоположение издательства: Russian Federation
Первая страница: 1873
Последняя страница: 1883
DOI: 10.1134/s107042802560367x
Аннотация: N-arylation of several adamantane-containing amines with iodobenzene and its derivatives containing electron-donor and electron-withdrawing groups in para- and meta-positions was studied under catalysis by non-immobilized copper and copper oxide nanoparticles. It was shown that the best yields of the target N-aryl derivatives are achieved using the CuNPs 10/80 nm/rac-BINOL catalytic system when carrying out the reaction in DMSO at 110°C, which turned out to be the most universal. In some cases, it is possible to use other ligands like 2-acetylcyclohexanone and 2-isobutyrylcyclohexanone, as well as DMF as a solvent at 140°C. The maximum yields of N-aryl derivatives exceeded 90%, the dependence of the arylation reaction efficiency on the structure of adamantane-containing amines was shown, however, the effect of substituents in the aryl ring was not so significant. The leaching of copper into the solution during the model reaction was studied, it was shown that the degree of leaching depends on the nature of the ligand used. For comparison purposes, N-heteroarylation of adamantaneamine with trifluoromethyl-substituted 2-bromopyridines was studied, it was found that in this reaction copper leaching occurs to a greater extent. Using TEM, electronography and EDX spectroscopy data, it was shown that 25 nm CuNPs are converted mainly into copper (I) oxide during the reaction, while the average size of the nanoparticles remains virtually unchanged.
Добавил в систему: Аверин Алексей Дмитриевич

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Copper and Copper Oxide Nanoparticles in the Synthesis of N-Arylamines of the Adamantane Seriesстатья

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