The role of Pd nanoparticles in ionic liquid in the Heck reaction

被引:344
作者
Cassol, CC [1 ]
Umpierre, AP [1 ]
Machado, G [1 ]
Wolke, SI [1 ]
Dupont, J [1 ]
机构
[1] Univ Fed Rio Grande do Sul, Inst Chem, Lab Mol Catalysis, BR-91501970 Porto Alegre, RS, Brazil
关键词
D O I
10.1021/ja0430043
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Pd(0) nanoparticles with ∼2 nm diameter, immobilized in 1-n-butyl-3-methylimidazolium hexafluorophosphate ionic liquid, are efficient catalyst precursors for coupling of aryl halides with n-butylacrylate. In situ TEM analysis of the ionic liquid catalytic solution after the catalytic reaction shows the formation of larger nanoparticles (∼6 nm). The palladium content in the organic phase during the arylation reaction was checked by ICP-AS and shows significant metal leaching (up 34%) from the ionic phase to the organic phase at low substrate conversions and drops to 5-8% leaching at higher conversions. These results strongly suggest that the Pd(0) nanoparticles serve as a reservoir of homogeneous" catalytic active species. Copyright © 2005 American Chemical Society."
引用
收藏
页码:3298 / 3299
页数:2
相关论文
共 38 条
[1]   Preparation of nanoparticulate metal catalysts in porous supports using an ionic liquid route;: hydrogenation and C-C coupling [J].
Anderson, K ;
Fernández, SC ;
Hardacre, C ;
Marr, PC .
INORGANIC CHEMISTRY COMMUNICATIONS, 2004, 7 (01) :73-76
[2]   Palladacyclic catalysts in C-C and C-heteroatom bond-forming reactions [J].
Bedford, RB .
CHEMICAL COMMUNICATIONS, 2003, (15) :1787-1796
[3]   The heck reaction as a sharpening stone of palladium catalysis [J].
Beletskaya, IP ;
Cheprakov, AV .
CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066
[4]   Palladium metal catalysts in Heck C-C coupling reactions [J].
Biffis, A ;
Zecca, M ;
Basato, M .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2001, 173 (1-2) :249-274
[5]   Pd nanoparticle catalyzed Heck arylation of 1,1-disubstituted alkenes in ionic liquids.: Study on factors affecting the regioselectivity of the coupling process [J].
Caló, V ;
Nacci, A ;
Monopoli, A ;
Detomaso, A ;
Iliade, P .
ORGANOMETALLICS, 2003, 22 (21) :4193-4197
[6]   Pd nanoparticles catalyzed stereospecific synthesis of β-aryl cinnamic esters in ionic liquids [J].
Caló, V ;
Nacci, A ;
Monopoli, A ;
Laera, S ;
Cioffi, N .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (07) :2929-2933
[7]   The Heck reaction in ionic liquids: A multiphasic catalyst system [J].
Carmichael, AJ ;
Earle, MJ ;
Holbrey, JD ;
McCormac, PB ;
Seddon, KR .
ORGANIC LETTERS, 1999, 1 (07) :997-1000
[8]   Synthesis of surface organopalladium intermediates in coupling reactions: The mechanistic insight [J].
Choudary, BM ;
Madhi, S ;
Kantam, ML ;
Sreedhar, B ;
Iwasawa, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (08) :2292-2293
[9]   Chloropalladated propargyl amine: A highly efficient phosphine-free catalyst precursor for the Heck reaction [J].
Consorti, CS ;
Zanini, ML ;
Leal, S ;
Ebeling, G ;
Dupont, J .
ORGANIC LETTERS, 2003, 5 (07) :983-986
[10]  
de Vries AHM, 2002, ADV SYNTH CATAL, V344, P996, DOI 10.1002/1615-4169(200210)344:9<996::AID-ADSC996>3.0.CO