Highly efficient and recyclable palladium catalyst anchored on organic-inorganic hybrid material: Application in the Heck reaction

被引：22
作者：
Liu, Hongqiang [1 ]
Wang, Lei [1 ,2 ]
Li, Pinhua [1 ]
机构：
[1] Huaibei Coal Teachers Coll, Dept Chem, Huaibei 235000, Anhui, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
来源：
SYNTHESIS-STUTTGART | 2008年 / 15期
基金：
中国国家自然科学基金;
关键词：
Heck reaction; organic-inorganic hybrid material; silica-anchored proline-palladium catalyst; heterogeneous catalysis; alkenes; aryl iodides; aryl bromides;
D O I：
10.1055/s-2008-1067161
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Palladium anchored on organic-inorganic (silica gel) hybrid materials behaves as a very efficient heterogeneous catalyst in the Fleck reaction. Iodoarenes and bromoarenes react smoothly with alkenes to afford the corresponding cross-coupling products in good to excellent yields under phosphine- and amine-free reaction conditions in the presence of a palladium anchored on L-proline-functionalized silica gel as catalyst. The silica-supported palladium catalyst can be recovered and recycled by simple filtration of the reaction solution, and used for more than 14 consecutive trials without significant loss of its catalytic activity.
引用
收藏
页码：2405 / 2411
页数：7
相关论文
共 78 条
  • [51] Accelerating effect induced by the structure of α-amino acid in the copper-catalyzed coupling reaction of aryl halides with α-amino acids.: Synthesis of benzolactam-V8
    Ma, DW
    Zhang, YD
    Yao, JC
    Wu, SH
    Tao, FG
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (48) : 12459 - 12467
  • [52] CuI-catalyzed coupling reaction of β-amino acids or esters with aryl halides at temperature lower than that employed in the normal Ullmann reaction.: Facile synthesis of SB-214857
    Ma, DW
    Xia, CF
    [J]. ORGANIC LETTERS, 2001, 3 (16) : 2583 - 2586
  • [53] First total synthesis of martinellic acid, a naturally occurring bradykinin receptor antagonist
    Ma, DW
    Xia, CF
    Jiang, JQ
    Zhang, JH
    [J]. ORGANIC LETTERS, 2001, 3 (14) : 2189 - 2191
  • [54] L-Proline promoted Ullmann-type coupling reactions of aryl iodides with indoles, pyrroles, imidazoles or pyrazoles
    Ma, DW
    Cai, Q
    [J]. SYNLETT, 2004, (01) : 128 - 130
  • [55] Pt and Pd nanoparticles immobilized on amine-functionalized zeolite: Excellent catalysts for hydrogenation and heck reactions
    Mandal, S
    Roy, D
    Chaudhari, RV
    Sastry, M
    [J]. CHEMISTRY OF MATERIALS, 2004, 16 (19) : 3714 - 3724
  • [56] Immobilization of copper in organic-inorganic hybrid materials: a highly efficient and reusable catalyst for the Ullmann diaryl etherification
    Miao, Tao
    Wang, Lei
    [J]. TETRAHEDRON LETTERS, 2007, 48 (01) : 95 - 99
  • [57] Phosphine-free hydrazone-Pd complex as the catalyst precursor for a Suzuki-Miyaura reaction under mild aerobic conditions
    Mino, T
    Shirae, Y
    Sakamoto, M
    Fujita, T
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (06) : 2191 - 2194
  • [58] Controlled synthesis of hydroxyapatite-supported palladium complexes as highly efficient heterogeneous catalysts
    Mori, K
    Yamaguchi, K
    Hara, T
    Mizugaki, T
    Ebitani, K
    Kaneda, K
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (39) : 11572 - 11573
  • [59] Di-2-pyridylmethylamine-based palladium complexes as new catalysts for Heck, Suzuki, and Sonogashira reactions in organic and aqueous solvents
    Nájera, C
    Gil-Moltó, J
    Karlstrom, S
    Falvello, LR
    [J]. ORGANIC LETTERS, 2003, 5 (09) : 1451 - 1454
  • [60] Catalytic performance and elution of Pd in the Heck reaction over zeolite-supported Pd cluster catalyst
    Okumura, K
    Nota, K
    Yoshida, K
    Niwa, M
    [J]. JOURNAL OF CATALYSIS, 2005, 231 (01) : 245 - 253
12345678