Nicotine functionalized-silica palladium (II) complex: a highly efficient, environmentally benign and recyclable nanocatalyst for C-C bond forming reactions under mild conditions

被引:5
作者
Hajipour, Abdol R. [1 ,2 ]
Tadayoni, Nayereh S. [1 ]
Mohammadsaleh, Fatemeh [1 ]
机构
[1] Isfahan Univ Technol, Dept Chem, Pharmaceut Res Lab, Esfahan 84156, Iran
[2] Univ Wisconsin, Sch Med, Dept Pharmacol, 1300 Univ Ave, Madison, WI 53706 USA
关键词
mizoroki-heck reaction; suzuki-miyaura reaction; magnetic nanoparticles; n-heterocyclic carbenes; CROSS-COUPLING REACTIONS; MULTIWALLED CARBON NANOTUBES; HETEROGENEOUS CATALYSIS; SONOGASHIRA REACTIONS; ROOM-TEMPERATURE; SUZUKI-MIYAURA; IONIC LIQUIDS; ARYL HALIDES; AEROBIC CONDITIONS; GREEN CHEMISTRY;
D O I
10.1002/aoc.3507
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
An environmentally friendly silica-grafted nicotine-based palladium(II) complex was successfully prepared and evaluated for the first time as novel and efficient nanocatalyst in C-C bond forming reactions. Grafted-nicotine in this catalytic system plays an important role, and as an effective ligand and a quaternary ammonium salt demonstrates an efficient stabilizing effect on the Pd(II) species by a synergistic effect of coordination and electrostatic interactions. The catalyst was well characterized by FT-IR, CHN, XRD, TEM, SEM-EDX, ICP and TG analysis, and demonstrated a highly efficient catalytic activity in the reaction system under phosphine-free and low Pd loading conditions, and the coupled products were produced in good to excellent yields. Furthermore, the catalyst can be easily recovered and reused without a significant loss of activity. Copyright (c) 2016 John Wiley & Sons, Ltd.
引用
收藏
页码:777 / 782
页数:6
相关论文
共 56 条
[1]   Highly efficient catalytic hydrodehalogenation of polychlorinated biphenyls (PCBs) [J].
Akzinnay, Said ;
Bisaro, Fabrice ;
Cazin, Catherine S. J. .
CHEMICAL COMMUNICATIONS, 2009, (38) :5752-5753
[2]  
[Anonymous], 2008, METAL CATALYZED CROS
[3]   Application of the palladium-catalyzed borylation/Suzuki coupling (BSC) reaction to the synthesis of biologically active biaryl lactams [J].
Baudoin, O ;
Cesario, M ;
Guénard, D ;
Guéritte, F .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (04) :1199-1207
[4]   The impact of nanoscience on heterogeneous catalysis [J].
Bell, AT .
SCIENCE, 2003, 299 (5613) :1688-1691
[5]   Base free aryl coupling of diazonium compounds and boronic esters: self-activation allowing an overall highly practical process [J].
Bonin, Helene ;
Delbrayelle, Dominique ;
Demonchaux, Patrice ;
Gras, Emmanuel .
CHEMICAL COMMUNICATIONS, 2010, 46 (15) :2677-2679
[6]   Pd nanoparticles as efficient catalysts for Suzuki and Stille coupling reactions of aryl halides in ionic liquids [J].
Calò, V ;
Nacci, A ;
Monopoli, A ;
Montingelli, F .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (15) :6040-6044
[7]   Synthesis of palladium nanocatalysts with cucurbit[n]uril as both a protecting agent and a support for Suzuki and Heck reactions [J].
Cao, Minna ;
Wei, Ye ;
Gao, Shuiying ;
Cao, Rong .
CATALYSIS SCIENCE & TECHNOLOGY, 2012, 2 (01) :156-163
[8]   Heterogeneous Catalysis for Tandem Reactions [J].
Climent, Maria J. ;
Corma, Avelino ;
Iborra, Sara ;
Sabater, Maria J. .
ACS CATALYSIS, 2014, 4 (03) :870-891
[9]   Palladium-Catalyzed Cross-Coupling of Styrenes with Aryl Methyl Ketones in Ionic Liquids: Direct Access to Cyclopropanes [J].
Cotugno, Pietro ;
Monopoli, Antonio ;
Ciminale, Francesco ;
Milella, Antonella ;
Nacci, Angelo .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (49) :13563-13567
[10]   Heterogeneous Catalysis for the Conversion of Sugars into Polymers [J].
Davis, Mark E. .
TOPICS IN CATALYSIS, 2015, 58 (7-9) :405-409