Pd Immobilized in Mesoporous Silica Particles as Recyclable Catalysts for Suzuki-Miyaura Coupling: Cooperative Effects Exerted by Co-Immobilized Amine Functionalities

被引：28

作者：

Dickschat, Arne T. ^{[1
]}

Surmiak, Sabrina ^{[1
]}

Studer, Armido ^{[1
]}

机构：

[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany

来源：

SYNLETT | 2013年 / 24卷 / 12期

关键词：

mesoporous silica nanoparticles; cooperative Pd catalysis; Suzuki coupling; catalyst immobilization; NITROXIDE EXCHANGE-REACTIONS; PALLADIUM COMPLEX; SUPPORTED PALLADIUM; CLICK CHEMISTRY; HECK REACTION; NANOPARTICLES; MCM-41; LIGAND; SONOGASHIRA; TRIAZOLE;

D O I：

10.1055/s-0033-1339183

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A bifunctional heterogeneous palladium catalyst bearing additional basic sites was successfully prepared by sequential Cu-catalyzed 1,3-dipolar alkyne-azide cycloaddition and thermal nitroxide-exchange reaction of surface-bound alkoxyamines. This catalyst shows high activity in the Suzuki-Miyaura cross-coupling. The additional basic functionality acts cooperatively since an analogous heterogeneous Pd catalyst lacking the amine functionality is less active. Such catalysts can be recycled up to ten times without loss of activity.

引用

页码：1523 / 1528

页数：6

共 40 条

[1] Kaiser oxime resin-derived palladacycle: A recoverable polymeric precatalyst in Suzuki-Miyaura reactions in aqueous media [J].

Alacid, Emilio ;

Najera, Carmen .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2009, 694 (11) :1658-1665

[2] Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure [J].

Barder, TE ;

Walker, SD ;

Martinelli, JR ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4685-4696

[3] "Clicking" Polymers or Just Efficient Linking: What Is the Difference? [J].

Barner-Kowollik, Christopher ;

Du Prez, Filip E. ;

Espeel, Pieter ;

Hawker, Craig J. ;

Junkers, Tanja ;

Schlaad, Helmut ;

Van Camp, Wim .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (01) :60-62

[4]

BARZ M, 1998, ANGEW CHEM, V110, P2380

[5] Site-specific immobilization of proteins at zeolite L crystals by nitroxide exchange reactions [J].

Becker, Maike ;

De Cola, Luisa ;

Studer, Armido .

CHEMICAL COMMUNICATIONS, 2011, 47 (12) :3392-3394

[6] Anchoring of palladium(II) in chemically modified mesoporous silica: An efficient heterogeneous catalyst for Suzuki cross-coupling reaction [J].

Bhunia, Susmita ;

Sen, Rupam ;

Koner, Subratanath .

INORGANICA CHIMICA ACTA, 2010, 363 (14) :3993-3999

[7] Polytriazoles as copper(I)-stabilizing ligands in catalysis [J].

Chan, TR ;

Hilgraf, R ;

Sharpless, KB ;

Fokin, VV .

ORGANIC LETTERS, 2004, 6 (17) :2853-2855

[8] Silica supported palladium-phosphine complex: recyclable catalyst for Suzuki-Miyaura cross-coupling reactions at ambient temperature [J].

Chen, Wei ;

Li, Pinhua ;

Wang, Lei .

TETRAHEDRON, 2011, 67 (02) :318-325

[9] The use of palladium nanoparticles supported with MCM-41 and basic (Al)MCM-41 mesoporous sieves in microwave-assisted Heck reaction [J].

Demel, Jan ;

Park, Sang-Eon ;

Cejka, Jiri ;

Stepnicka, Petr .

CATALYSIS TODAY, 2008, 132 (1-4) :63-67

[10] A new functionalized mesoporous matrix supported Pd(II)-Schiff base complex: an efficient catalyst for the Suzuki-Miyaura coupling reaction [J].

Dhara, Koushik ;

Sarkar, Krishanu ;

Srimani, Dipankar ;

Saha, Subrata Kumar ;

Chattopadhyay, Pabitra ;

Bhaumik, Asim .

DALTON TRANSACTIONS, 2010, 39 (28) :6395-6402

← 1 2 3 4 →