Cu(II)-silsesquioxanes as efficient precatalysts for Chan-Evans-Lam coupling

Two cage copper(II)silsesquioxanes, namely, tricopper complex (PhSiO1.5)8(CuO)3(TMEDA)2*(MeCN)3 Cu-1 and hexacopper complex (MeSiO1,5)12(CuO)6(Py)6*TMEDA Cu-2 were synthesized (in 30% and 16% yield, respectively) via TMEDA-assisted reactions (TMEDA = tetramethylethylenediamine). Structural features of both products were established by X-ray diffraction study. Complexes Cu-1 and Cu-2, along with some Cu(II)-silsesquioxanes reported earlier, were evaluated for the first time as precatalysts for the homogeneous Chan-Evans-Lam (CEL) O-arylation of benzoic acids (the highest yield of phenylbenzoic ester was 84%). Observed catalytic activity was superior to reference catalyst Cu(OAc)2*H2O. Finally, an application of coppersilsesquioxanes allowed to observe the first example of C-O CEL coupling under microwave activation characterized by (i) reduced loading of copper, (ii) low amount of added base, (iii) minimization of the time of reaction. © 2019 Elsevier B.V.

Язык
Английский
Статус
Опубликовано
Номер
121022
Том
906
Год
2020
Организации
  • 1 Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilova str., 28, Moscow, 119991, Russian Federation
  • 2 Peoples’ Friendship University of Russia, Miklukho-Maklay Str., 6, Moscow, 117198, Russian Federation
  • 3 Institut des Biomolécules Max Mousseron (IBMM), UMR 5247, CNRS, Université de Montpellier ENSCM, Site Triolet, Place Eugène Bataillon, Montpellier Cedex 534095, France
  • 4 Boreskov Institute of Catalysis SB RAS, Akad. Lavrentieva Ave., 5, Novosibirsk, 630090, Russian Federation
  • 5 National Research Center “Kurchatov Institute”, Akademika Kurchatova pl., 1, Moscow, Russian Federation
Ключевые слова
Chan-Evans-Lam coupling; Copper complexes; Metallasilsesquioxanes; X-ray
Дата создания
10.02.2020
Дата изменения
10.02.2020
Постоянная ссылка
https://repository.rudn.ru/ru/records/article/record/56534/