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

被引：22

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

[71] Aerobic Carbon-Carbon Bond Cleavage of Alkenes to Aldehydes Catalyzed by First-Row Transition-Metal-Substituted Polyoxometalates in the Presence of Nitrogen Dioxide [J].

Rubinstein, Amir ;

Jimenez-Lozanao, Pablo ;

Carbo, Jorge J. ;

Poblet, Josep M. ;

Neumann, Ronny .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (31) :10941-10948

[72] Metal-free synthesis of aryl esters by coupling aryl carboxylic acids and aryl boronic acids [J].

Ruso, Jayaraman Sembian ;

Rajendiran, Nagappan ;

Kumaran, Rajendran Senthil .

TETRAHEDRON LETTERS, 2014, 55 (15) :2345-2347

[73] Structural diversity of copper(II) amino alcoholate complexes [J].

Seppala, Petri ;

Sillanpaa, Reijo ;

Lehtonen, Ari .

COORDINATION CHEMISTRY REVIEWS, 2017, 347 :98-114

[74] Metallosiloxanes containing period 5 transition metals: synthesis and X-ray studies of three cadmium siloxanes [J].

Sergienko, Natalia V. ;

Korlyukov, Alexander A. ;

Arkhipov, Dmitry E. ;

Novikov, Valentin V. ;

Eskova, Marina A. ;

Zavin, Boris G. .

MENDELEEV COMMUNICATIONS, 2016, 26 (04) :344-346

[75] Electrocatalytic Water Oxidation by a Dinuclear Copper Complex in a Neutral Aqueous Solution [J].

Su, Xiao-Jun ;

Gao, Meng ;

Jiao, Lei ;

Liao, Rong-Zhen ;

Siegbahn, Per E. M. ;

Cheng, Jin-Pei ;

Zhang, Ming-Tian .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (16) :4909-4914

[76] Copper-Catalyzed N- and O-Alkylation of Amines and Phenols using Alkylborane Reagents [J].

Sueki, Shunsuke ;

Kuninobu, Yoichiro .

ORGANIC LETTERS, 2013, 15 (07) :1544-1547

[77] Catalytic Activity of Polynuclear vs. Dinuclear Aroylhydrazone Cu(II) Complexes in Microwave-Assisted Oxidation of Neat Aliphatic and Aromatic Hydrocarbons [J].

Sutradhar, Manas ;

Barman, Tannistha Roy ;

Pombeiro, Armando J. L. ;

Martins, Luisa M. D. R. S. .

MOLECULES, 2019, 24 (01)

[78] Cu24O24Si8R8: Organic Soluble 56-Membered Copper(I) Siloxane Cage and Its Use in Homogeneous Catalysis [J].

Tan, Gengwen ;

Yang, Ying ;

Chu, Chenhui ;

Zhu, Hongping ;

Roesky, Herbert W. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (35) :12231-12233

[79] Spectroscopic Studies of the Chan-Lam Amination: A Mechanism Inspired Solution to Boronic Ester Reactivity [J].

Vantourout, Julien C. ;

Miras, Haralampos N. ;

Isidro-Llobet, Albert ;

Sproules, Stephen ;

Watson, Allan J. B. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (13) :4769-4779

[80] Alkane oxidation with peroxides catalyzed by cage-like copper(II) silsesquioxanes [J].

Vinogradov, Mikhail M. ;

Kozlov, Yuriy N. ;

Bilyachenko, Alexey N. ;

Nesterov, Dmytro S. ;

Shul'pina, Lida S. ;

Zubavichus, Yan V. ;

Pombeiro, Armando J. L. ;

Levitsky, Mikhail M. ;

Yalymov, Alexey I. ;

Shul'pin, Georgiy B. .

NEW JOURNAL OF CHEMISTRY, 2015, 39 (01) :187-199

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