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

被引：21

作者：

Astakhov, G. S. ^{[1
,2
]}

Levitsky, M. M. ^{[1
]}

Bantreil, X. ^{[3
]}

Lamaty, F. ^{[3
]}

Khrustalev, V. N. ^{[2
]}

Zubavichus, Y. V. ^{[4
]}

Dorovatovskii, P. V. ^{[5
]}

Shubina, E. S. ^{[1
]}

Bilyachenko, A. N. ^{[1
,2
]}

机构：

[1] Russian Acad Sci, Nesmeyanov Inst Organoelement Cpds, Vavilova Str 28, Moscow 119991, Russia

[2] Peoples Friendship Univ Russia, Miklukho Maklay Str 6, Moscow 117198, Russia

[3] Univ Montpellier, IBMM, CNRS, UMR 5247,ENSCM, Site Triolet,Pl Eugene Bataillon, F-34095 Montpellier 5, France

[4] RAS, Boreskov Inst Catalysis SB, Akad Lavrentieva Ave 5, Novosibirsk 630090, Russia

[5] Kurchatov Inst, Natl Res Ctr, Akad Kurchatova Pl 1, Moscow, Russia

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2020年 / 906卷 / 906期

关键词：

Copper complexes; Chan-Evans-Lam coupling; Metallasilsesquioxanes; X-ray; CATALYTIC-ACTIVITY; ARYLBORONIC ACIDS; TRANSITION-METAL; COPPER COMPLEX; SILSESQUIOXANE CHEMISTRY; HETEROGENEOUS CATALYST; ORGANIC FRAMEWORK; CARBOXYLIC-ACIDS; BOND-CLEAVAGE; BORONIC ACIDS;

D O I：

10.1016/j.jorganchem.2019.121022

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

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. (C) 2019 Elsevier B.V. All rights reserved.

引用

页数：7

共 84 条

[1]

Abbati GL, 2002, ANGEW CHEM INT EDIT, V41, P4517, DOI 10.1002/1521-3773(20021202)41:23<4517::AID-ANIE4517>3.0.CO

[2]

2-G

[3] Self-assembly of high-nuclearity metal clusters:: Programmed expansion of a metallasiloxane cage to an octacopper(II) cluster [J].

Abbati, GL ;

Cornia, A ;

Caneschi, A ;

Fabretti, AC ;

Mortalò, C .

INORGANIC CHEMISTRY, 2004, 43 (15) :4540-4542

[4] Accessing the inaccessible: discrete multinuclear coordination complexes and selective anion binding attainable only by tethering ligands together [J].

Ahmed, Basil M. ;

Mezei, Gellert .

CHEMICAL COMMUNICATIONS, 2017, 53 (06) :1029-1032

[5] Cu3(BTC)2 metal-organic framework catalyzed N-arylation of benzimidazoles and imidazoles with phenylboronic acid [J].

Anbu, Nagaraj ;

Dhakshinamoorthy, Amarajothi .

JOURNAL OF INDUSTRIAL AND ENGINEERING CHEMISTRY, 2018, 65 :120-126

[6] Tridecanuclear CuII11Na2 Cagelike Silsesquioxanes [J].

Astakhov, Grigorii S. ;

Bilyachenko, Alexey N. ;

Levitsky, Mikhail M. ;

Korlyukov, Alexander A. ;

Zubavichus, Yan, V ;

Dorovatovskii, Pavel, V ;

Khrustalev, Victor N. ;

Vologzhanina, Anna V. ;

Shubina, Elena S. .

CRYSTAL GROWTH & DESIGN, 2018, 18 (09) :5377-5384

[7] High-Cluster (Cu9) Cage Silsesquioxanes: Synthesis, Structure, and Catalytic Activity [J].

Astakhov, Grigorii S. ;

Bilyachenko, Alexey N. ;

Korlyukov, Alexander A. ;

Levitsky, Mikhail M. ;

Shul'pina, Lidia S. ;

Bantreil, Xavier ;

Lamaty, Frederic ;

Vologzhanina, Anna V. ;

Shubina, Elena S. ;

Dorovatovskii, Pavel, V ;

Nesterov, Dmytro S. ;

Pombeiro, Armando J. L. ;

Shul'pin, Georgiy B. .

INORGANIC CHEMISTRY, 2018, 57 (18) :11524-11529

[8] Copper(II) Complexes of a Hexadentate Mixed-Donor N3S3 Macrobicyclic Cage: Facile Rearrangements and Interconversions [J].

Bell, Craig A. ;

Bernhardt, Paul V. ;

Gahan, Lawrence R. ;

Martinez, Manuel ;

Monteiro, Michael J. ;

Rodriguez, Carlos ;

Sharrad, Clint A. .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (10) :3166-3175

[9] Synthesis, characterization and catalytic properties of dinuclear complexes of copper(II) and nickel(II): Oxidation of cyclohexane, toluene and cyclopentane [J].

Bhattacharjee, Aradhita ;

Dey, Sudipto ;

Roy, Partha .

INORGANICA CHIMICA ACTA, 2019, 490 :93-103

[10] Trinuclear copper(I) complexes with triscarbene ligands: catalysis of C-N and C-C coupling reactions [J].

Biffis, Andrea ;

Tubaro, Cristina ;

Scattolin, Elena ;

Basato, Marino ;

Papini, Grazia ;

Santini, Carlo ;

Alvarez, Eleuterio ;

Conejero, Salvador .

DALTON TRANSACTIONS, 2009, (35) :7223-7229

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