Suzuki-Miyaura coupling under air in water promoted by polymer supported palladium nanoparticles

被引:44
作者
Dell'Anna, Maria Michela [1 ]
Mali, Matilda [1 ]
Mastrorilli, Piero [1 ,2 ]
Rizzuti, Antonino [1 ]
Ponzoni, Chiara [3 ]
Leonelli, Cristina [3 ]
机构
[1] Politecn Bari, DICATECh, I-70125 Bari, Italy
[2] Ist Chim Composti Organometall ICCOM CNR, Consiglio Nazl Ric, I-70125 Bari, Italy
[3] Univ Modena & Reggio Emilia, Dipartimento Ingn Mat & Ambiente, I-41125 Modena, Italy
关键词
Suzuki-Miyaura coupling; Palladium supported nanoparticles; Green solvent; Recyclable catalyst; HETEROGENEOUS CATALYSIS; REUSABLE CATALYST; PD NANOPARTICLES; MIZOROKI-HECK; EFFICIENT; GREEN; NANOCATALYSTS; PRECATALYSTS; COMPLEXES;
D O I
10.1016/j.molcata.2012.09.022
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Suzuki couplings of aryl bromides were efficiently performed by a polymer supported palladium catalyst under air in water at 100 degrees C without additives. In the case of activated aryl chlorides the reactions proceeded smoothly in the presence of a suitable phase transfer agent. The catalyst was active and recyclable for at least five times. Atomic absorption analyses revealed that the metal content in the polymeric support did not significantly decrease with the cycles while inductively coupled plasma analyses revealed that the palladium amount both in the mother liquors and in the organic products after reactions was lower than 500 ppb. The activity of the mother liquors has been investigated in detail. A transmission electron microscopy study of the supported catalyst before, during and after duty is also described. (c) 2012 Elsevier B.V. All rights reserved.
引用
收藏
页码:186 / 194
页数:9
相关论文
共 68 条
[1]   Polymers for Green C-C Couplings [J].
Albeniz, Ana C. ;
Carrera, Nora .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2011, (15) :2347-2360
[2]   PdO hydrate as an efficient and recyclable catalyst for the Suzuki-Miyaura reaction in water/ethanol at room temperature [J].
Amoroso, Francesco ;
Colussi, Sara ;
Del Zotto, Alessandro ;
Llorca, Jordi ;
Trovarelli, Alessandro .
CATALYSIS COMMUNICATIONS, 2011, 12 (06) :563-567
[3]   An efficient and reusable catalyst based on Pd/CeO2 for the room temperature aerobic Suzuki-Miyaura reaction in water/ethanol [J].
Amoroso, Francesco ;
Colussi, Sara ;
Del Zotto, Alessandro ;
Llorca, Jordi ;
Trovarelli, Alessandro .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2010, 315 (02) :197-204
[4]   Efficient, Selective, and Recyclable Palladium Catalysts in Carbon-Carbon Coupling Reactions [J].
Arpad Molnar .
CHEMICAL REVIEWS, 2011, 111 (03) :2251-2320
[5]   Nanoparticles as recyclable catalysts: The frontier between homogeneous and heterogeneous catalysis [J].
Astruc, D ;
Lu, F ;
Aranzaes, JR .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (48) :7852-7872
[6]   Palladium nanoparticles as efficient green homogeneous and heterogeneous carbon-carbon coupling precatalysts: A unifying view [J].
Astruc, Didier .
INORGANIC CHEMISTRY, 2007, 46 (06) :1884-1894
[7]   Pd nanoparticles for C-C coupling reactions [J].
Balanta, Angelica ;
Godard, Cyril ;
Claver, Carmen .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :4973-4985
[8]   The heck reaction as a sharpening stone of palladium catalysis [J].
Beletskaya, IP ;
Cheprakov, AV .
CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066
[9]   Recoverable and recyclable chiral organic catalysts [J].
Benaglia, Maurizio .
NEW JOURNAL OF CHEMISTRY, 2006, 30 (11) :1525-1533
[10]   Nitrogen-rich porous covalent imine network (CIN) material as an efficient catalytic support for C-C coupling reactions [J].
Bhunia, Manas K. ;
Das, Swapan K. ;
Pachfule, Pradip ;
Banerjee, Rahul ;
Bhaumik, Asim .
DALTON TRANSACTIONS, 2012, 41 (04) :1304-1311