One "Click" to controlled bifunctional supported catalysts for the Cu/TEMPO-catalyzed aerobic oxidation of alcohols

被引:37
作者
Fernandes, Antony E. [1 ,2 ]
Riant, Olivier [1 ]
Jonas, Alain M. [1 ]
Jensen, Klavs F. [2 ]
机构
[1] Catholic Univ Louvain, Inst Condensed Matter & Nanosci, B-1348 Louvain La Neuve, Belgium
[2] MIT, Dept Chem Engn, Cambridge, MA 02139 USA
来源
RSC ADVANCES | 2016年 / 6卷 / 43期
关键词
MESOPOROUS SILICA NANOPARTICLES; HETEROGENEOUS SYNERGISTIC CATALYSIS; TSUJI-TROST REACTION; COOPERATIVE CATALYSIS; FUNCTIONAL-GROUPS; SELECTIVE OXIDATION; REUSABLE CATALYSTS; PALLADIUM COMPLEX; TERMINAL ALKYNES; SUZUKI-MIYAURA;
D O I
10.1039/c6ra05026c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A simple and reliable methodology is described for the preparation of heterogeneous bifunctional catalysts with a high control over surface composition. The strategy relies on the grafting of a mix of catalytic components from an azide-functionalized silica platform using the CuAAC reaction. The resulting finely engineered supported catalysts are employed in the model Cu/TEMPO-catalyzed aerobic oxidation of benzylic alcohol.
引用
收藏
页码:36602 / 36605
页数:4
相关论文
共 63 条
[1]   Copper-catalyzed aerobic oxidation of alcohols under fluorous biphasic conditions [J].
Betzemeier, B ;
Cavazzini, M ;
Quici, S ;
Knochel, P .
TETRAHEDRON LETTERS, 2000, 41 (22) :4343-4346
[2]   A biphasic oxidation of alcohols to aldehydes and ketones using a simplified packed-bed microreactor [J].
Bogdan, Andrew ;
McQuade, D. Tyler .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2009, 5
[3]   Cooperative Catalysis with Acid-Base Bifunctional Mesoporous Silica: Impact of Grafting and Co-condensation Synthesis Methods on Material Structure and Catalytic Properties [J].
Brunelli, Nicholas A. ;
Venkatasubbaiah, Krishnan ;
Jones, Christopher W. .
CHEMISTRY OF MATERIALS, 2012, 24 (13) :2433-2442
[4]   Enantioselective Heterogeneous Synergistic Catalysis for Asymmetric Cascade Transformations [J].
Deiana, Luca ;
Ghisu, Lorenza ;
Afewerki, Samson ;
Verho, Oscar ;
Johnston, Eric V. ;
Hedin, Niklas ;
Bacsik, Zoltan ;
Cordova, Armando .
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (11-12) :2485-2492
[5]   Pd Immobilized in Mesoporous Silica Particles as Recyclable Catalysts for Suzuki-Miyaura Coupling: Cooperative Effects Exerted by Co-Immobilized Amine Functionalities [J].
Dickschat, Arne T. ;
Surmiak, Sabrina ;
Studer, Armido .
SYNLETT, 2013, 24 (12) :1523-1528
[6]   Bifunctional mesoporous silica nanoparticles as cooperative catalysts for the Tsuji-Trost reaction - tuning the reactivity of silica nanoparticles [J].
Dickschat, Arne T. ;
Behrends, Frederik ;
Surmiak, Sabrina ;
Weiss, Mark ;
Eckert, Hellmut ;
Studer, Armido .
CHEMICAL COMMUNICATIONS, 2013, 49 (22) :2195-2197
[7]   Preparation of Bifunctional Mesoporous Silica Nanoparticles by Orthogonal Click Reactions and Their Application in Cooperative Catalysis [J].
Dickschat, Arne T. ;
Behrends, Frederik ;
Buehner, Martin ;
Ren, Jinjun ;
Weiss, Mark ;
Eckert, Hellmut ;
Studer, Armido .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (52) :16689-16697
[8]   Cu(II)-nitroxyl radicals as catalytic galactose oxidase mimics [J].
Dijksman, A ;
Arends, IWCE ;
Sheldon, RA .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (18) :3232-3237
[9]   Effects of Thickness and Grafting Density on the Activity of Polymer-Brush-Immobilized Tris(triazolyl) Copper(I) Catalysts [J].
Fernandes, Antony E. ;
Ye, Qian ;
Collard, Laurent ;
Le Duff, Cecile ;
d'Haese, Cecile ;
Deumer, Gladys ;
Haufroid, Vincent ;
Nysten, Bernard ;
Riant, Olivier ;
Jonas, Alain M. .
CHEMCATCHEM, 2015, 7 (05) :856-864
[10]   Application of CuAAC for the covalent immobilization of homogeneous catalysts [J].
Fernandes, Antony E. ;
Jonas, Alain M. ;
Riant, Olivier .
TETRAHEDRON, 2014, 70 (09) :1709-1731