Efficient Click-Polymer-Stabilized Palladium Nanoparticle Catalysts for Suzuki-Miyaura Reactions of Bromoarenes and Reduction of 4-Nitrophenol in Aqueous Solvents

被引:28
作者
Deraedt, Christophe [1 ]
Salmon, Lionel [2 ,3 ]
Ruiz, Jaime [1 ]
Astruc, Didier [1 ]
机构
[1] Univ Bordeaux, ISM, UMR CNRS 5255, F-33405 Talence, France
[2] CNRS, LCC, F-31077 Toulouse, France
[3] Univ Toulouse, F-31077 Toulouse, France
关键词
bromoarenes; catalysis; click chemistry; green chemistry; 4-nitrophenol; palladium nanoparticles; polymers; Suzuki-Miyaura reaction; CROSS-COUPLING REACTIONS; HIGHLY EFFICIENT; HETEROGENEOUS CATALYSIS; SUPPORTED PALLADIUM(0); REUSABLE CATALYST; PD NANOPARTICLES; HECK REACTION; IONIC-LIQUID; ARYL; HOLLOW;
D O I
10.1002/adsc.201300633
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Palladium nanoparticles (size=1.60.3nm) stabilized by a polyethylene glycol containing triazolyl rings, synthesized by click reaction in water, are efficient catalysts for the Suzuki-Miyaura coupling of bromoarenes in aqueous ethanol and the borohydride reduction of 4-nitrophenol in water. Turnover numbers (TONs) reach 99,000 and turnover frequencies (TOFs) are up to 198,000h(-1) for the CC cross coupling reactions in water/ethanol.
引用
收藏
页码:2992 / 3001
页数:10
相关论文
共 63 条
[1]   Use of "homeopathic" ligand-free palladium as catalyst for aryl-aryl coupling reactions [J].
Alimardanov, A ;
de Vondervoort, LSV ;
de Vries, AHM ;
de Vries, JG .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) :1812-1817
[2]  
[Anonymous], 2008, METAL CATALYZED CROS
[3]   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
[4]   Metallodendritic catalysis for redox and carbon-carbon bond formation reactions:: A step towards green chemistry [J].
Astruc, D ;
Heuzé, K ;
Gatard, S ;
Méry, D ;
Nlate, S ;
Plault, L .
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (2-3) :329-338
[5]  
Astruc D., 2008, NANOPARTICLES CATALY
[6]  
Astruc D., 2007, ORGANOMETALLIC CHEM
[7]  
Astruc D., 2005, Angew. Chem, V117, P8062, DOI DOI 10.1002/ange.200500766
[8]   The heck reaction as a sharpening stone of palladium catalysis [J].
Beletskaya, IP ;
Cheprakov, AV .
CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066
[9]   Palladium catalysts for the Suzuki cross-coupling reaction: An overview of recent advances [J].
Bellina, F ;
Carpita, A ;
Rossi, R .
SYNTHESIS-STUTTGART, 2004, (15) :2419-2440
[10]   Effects of the Material Structure on the Catalytic Activity of Peptide-Templated Pd Nanomaterials [J].
Bhandari, Rohit ;
Knecht, Marc R. .
ACS CATALYSIS, 2011, 1 (02) :89-98