Bifunctional mesoporous silica nanoparticles as cooperative catalysts for the Tsuji-Trost reaction - tuning the reactivity of silica nanoparticles

被引:60
作者
Dickschat, Arne T. [1 ]
Behrends, Frederik [2 ]
Surmiak, Sabrina [1 ]
Weiss, Mark [2 ]
Eckert, Hellmut [2 ]
Studer, Armido [1 ]
机构
[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany
[2] Univ Munster, Inst Phys Chem, D-48149 Munster, Germany
关键词
PALLADIUM COMPLEX; IMMOBILIZATION; SURFACE;
D O I
10.1039/c3cc00235g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Bifunctional mesoporous silica nanoparticles (MSNs) bearing Pd-complexes and additional basic sites were prepared and tested as cooperative active catalysts in the Tsuji-Trost allylation of ethyl acetoacetate. Functionalization of the MSNs was realized by postmodification using click-chemistry. The selectivity of mono versus double allylation was achieved by control of reaction temperature and the nature of the catalyst.
引用
收藏
页码:2195 / 2197
页数:3
相关论文
共 20 条
[1]  
[Anonymous], 2010, ANGEW CHEM
[2]  
Baba T., 2012, ANGEW CHEM, V124, P8141
[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]   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
[5]   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
[6]  
Huang Y., 2011, ANGEW CHEM, V123, P687
[7]  
Kolb H.C., 2001, ANGEW CHEM, V113, P2056, DOI 10.1002/1521-3757(20010601)113:11
[8]   Heterogeneous copper-free Sonogashira coupling reaction of terminal alkynes with aryl halides over a quinoline-2-carboimine palladium complex immobilized on MCM-41 [J].
Komura, Kenichi ;
Nakamura, Hideki ;
Sugi, Yoshihiro .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2008, 293 (1-2) :72-78
[9]   Immobilization of dipyridyl complex to magnetic nanoparticle via click chemistry as a recyclable catalyst for Suzuki cross-coupling reactions [J].
Lv, Guanghua ;
Mai, Wenpeng ;
Jin, Rizhe ;
Gao, Lianxun .
SYNLETT, 2008, (09) :1418-1422
[10]   Organized surface functional groups: Cooperative catalysis via thiol/sulfonic acid pairing [J].
Margelefsky, Eric L. ;
Zeidan, Ryan K. ;
Dufaud, Veronique ;
Davis, Mark E. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (44) :13691-13697