Copper catalysis in the synthesis of N-naphthyl and N-quinolinyl derivatives of adamantane-containing amines

Kuliukhina, D.S.; Averin, A.D.; Abel, A.S.; Maloshitskaya, O.A.; Savelyev, E.N.; Orlinson, B.S.; Novakov, I.A.; Beletskaya, I.P.

Информация о цитировании статьи получена из Scopus
Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 15 февраля 2024 г.

Авторы: Kuliukhina D.S., Averin A.D., Abel A.S., Maloshitskaya O.A., Savelyev E.N., Orlinson B.S., Novakov I.A., Beletskaya I.P.
Журнал: Russian Chemical Bulletin
Том: 72
Номер: 11
Год издания: 2023
Издательство: Springer Nature
Местоположение издательства: Switzerland
Первая страница: 2612
Последняя страница: 2623
DOI: 10.1007/s11172-023-4065-x
Аннотация: N-(Het)arylation of adamantane-containing amines with halonaphthalenes and haloquinolines catalyzed by either CuI or copper nanoparticles with an average size of 25 nm in the presence of 2-isobutyrylcyclohexanone, rac-BINOL, and l-proline as a ligand and Cs2CO3 as a base in DMSO at 110 °C was studied. The reactions proceed smoothly with 2-iodonaphthalene and 6-iodoquinoline, the possibility of successful reactions with 6- and 3-bromoquinolines was also shown. In the case of 1-bromonaphthalene, 5- and 8-bromoquinolines, only Pd-catalyzed amination can provide the high yields of the products. An alternative possibility of C(sp2)—N bond formation was studied employing the Chan—Lam reaction with of 2-naphthaleneboronic acid and pinacolates of 6- and 3-quinolineboronic acids.
Добавил в систему: Абель Антон Сергеевич

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Copper catalysis in the synthesis of N-naphthyl and N-quinolinyl derivatives of adamantane-containing aminesстатья

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