Size controlled synthesis of Pd nanoparticles in water and their catalytic application in C-C coupling reactions

被引:126
作者
Sawoo, Sudeshna [1 ]
Srimani, Dipankar [1 ]
Dutta, Piyali [1 ]
Lahiri, Rima [1 ]
Sarkar, Amitabha [1 ]
机构
[1] Indian Assoc Cultivat Sci, Dept Organ Chem, Kolkata 700032, India
关键词
Pd nanoparticle; Fischer carbene complex; PEG; Water; C-C coupling; SUZUKI-MIYAURA REACTION; LIGAND-FREE PALLADIUM; COPPER-FREE; HECK REACTIONS; IONIC LIQUIDS; ARYL HALIDES; RECYCLABLE CATALYST; SONOGASHIRA REACTION; PHOSPHINE-LIGANDS; BOND FORMATIONS;
D O I
10.1016/j.tet.2009.03.062
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Catalytically active Pd nanoparticles have been synthesized in water by a novel reduction of Pd(II) with a Fischer carbene complex where polyethylene glycol (PEG) was used as stabilizer. PEG molecules wrap around the nanoparticles to impart stability and prevent agglomeration, yet leave enough surface area available on the nanoparticle for catalytic activity. Our method is superior to others in terms of rapid generation and stabilization of Pd nanoparticles in water with a cheap, readily available PEG stabilizer. The size of the nanoparticles generated can be controlled by the concentration of PEG in water medium. The size decreased with the increase in the PEG: Pd ratio. This aqueous nano-sized I'd is a highly efficient catalyst for Suzuki, Heck, Sonogashira, and Stille reaction. Water is Used as the only solvent for the coupling reactions. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4367 / 4374
页数:8
相关论文
共 115 条
[11]   Selective Pd-catalyzed oxidative coupling of anilides with olefins through C-H bond activation at room temperature [J].
Boele, MDK ;
van Strijdonck, GPF ;
de Vries, AHM ;
Kamer, PCJ ;
de Vries, JG ;
van Leeuwen, PWNM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (08) :1586-1587
[12]  
Brandsma L., 1998, APPL TRANSITION META
[13]   Chemistry and properties of nanocrystals of different shapes [J].
Burda, C ;
Chen, XB ;
Narayanan, R ;
El-Sayed, MA .
CHEMICAL REVIEWS, 2005, 105 (04) :1025-1102
[14]   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
[15]   PALLADIUM-CATALYZED ALKYLATIONS IN AQUEOUS-MEDIA [J].
CASALNUOVO, AL ;
CALABRESE, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) :4324-4330
[16]   SYNTHESIS OF ARYL-SUBSTITUTED AND VINYL-SUBSTITUTED ACETYLENE DERIVATIVES BY USE OF NICKEL AND PALLADIUM COMPLEXES [J].
CASSAR, L .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 93 (02) :253-257
[17]   Selected patented cross-coupling reaction technologies [J].
Corbet, Jean-Pierre ;
Mignani, Gerard .
CHEMICAL REVIEWS, 2006, 106 (07) :2651-2710
[18]   Comparison between polyethylenglycol and imidazolium ionic liquids as solvents for developing a homogeneous and reusable palladium catalytic system for the Suzuki and Sonogashira coupling [J].
Corma, A ;
García, H ;
Leyva, A .
TETRAHEDRON, 2005, 61 (41) :9848-9854
[19]   Polyethyleneglycol as scaffold and solvent for reusable C-C coupling homogeneous Pd catalysts [J].
Corma, Avelino ;
Garcia, Hermenegildo ;
Leyva, Antonio .
JOURNAL OF CATALYSIS, 2006, 240 (02) :87-99
[20]   Bulk and fine chemicals via aqueous biphasic catalysis [J].
Cornils, B .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1999, 143 (1-3) :1-10