Palladium(0) nanoparticles formed in situ in the Suzuki-Miyaura reaction: The effect of a palladium(II) precursor

被引:46
作者
Borkowski, T. [1 ]
Trzeciak, A. M. [1 ]
Bukowski, W. [2 ]
Bukowska, A. [2 ]
Tylus, W. [3 ]
Kepinski, L. [4 ]
机构
[1] Univ Wroclaw, Fac Chem, PL-50383 Wroclaw, Poland
[2] Rzeszow Univ Technol, Fac Chem, PL-35959 Rzeszow, Poland
[3] Wroclaw Univ Technol, Inst Inorgan Technol, PL-50370 Wroclaw, Poland
[4] Polish Acad Sci, Inst Low Temp & Struct Res, PL-50950 Wroclaw, Poland
关键词
Palladium; Nanoparticles; Suzuki-Miyaura; Immobilized catalyst; XPS; CROSS-COUPLING REACTIONS; HECK REACTION; C-C; ARYL CHLORIDES; CATALYSTS; PD; EFFICIENT; TEMPERATURE; PALLADACYCLES; POLYMER;
D O I
10.1016/j.apcata.2010.02.004
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
Two palladium catalyst precursors were prepared by immobilizing PdCl(2) and Pd(OAc)(2) on cyclohexyldiamine-modified glycidyl methacrylate polymer (GMA-CHDA) and used in the Suzuki-Miyaura reaction (80 degrees C, 2 h) without any pre-treatment. Using the TEM, SEM, EDS, and XPS methods, we were able to characterize the Pd(0) nanoparticles formed in situ during the catalytic process. The catalyst obtained from Pd(OAc)(2) (P(2)) contained Pd(0) nanoparticles with a diameter of 3-5 nm, whereas much bigger agglomerates were found for P(1), which had been obtained from PdCl(2). The P(2) catalyst exhibited much better catalytic performance than PI. pointing to an important role of the palladium precursor in the preparation of the catalyst. (C) 2010 Elsevier B.V. All rights reserved.
引用
收藏
页码:83 / 89
页数:7
相关论文
共 45 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]   Palladium-imidazolium carbene catalyzed aryl, vinyl, and alkyl Suzuki-Miyaura cross coupling [J].
Andrus, MB ;
Song, C .
ORGANIC LETTERS, 2001, 3 (23) :3761-3764
[3]   A reassessment of the transition-metal free Suzuki-type coupling methodology [J].
Arvela, RK ;
Leadbeater, NE ;
Sangi, MS ;
Williams, VA ;
Granados, P ;
Singer, RD .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (01) :161-168
[4]   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
[5]   The development of palladium catalysts for C-C and C-heteroatom bond forming reactions of aryl chloride substrates [J].
Bedford, RB ;
Cazin, CSJ ;
Holder, D .
COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2283-2321
[6]   Di- and tri-alkylphosphine adducts of S-donor palladacycles as catalysts in the Suzuki coupling of aryl chlorides [J].
Bedford, RB ;
Cazin, CSJ ;
Hursthouse, MB ;
Light, ME ;
Scordia, EJM .
DALTON TRANSACTIONS, 2004, (22) :3864-3868
[7]   The heck reaction as a sharpening stone of palladium catalysis [J].
Beletskaya, IP ;
Cheprakov, AV .
CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066
[8]   PALLADACYCLES AS EFFICIENT CATALYSTS FOR ARYL COUPLING REACTIONS [J].
BELLER, M ;
FISCHER, H ;
HERRMANN, WA ;
OFELE, K ;
BROSSMER, C .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (17) :1848-1849
[9]  
Beller M., 2004, TRANSITION METALS OR
[10]   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