Tandem catalytic condensation and hydrogenation processes in ionic liquids

被引：16
作者：
Baidossi, M
Joshi, AV
Mukhopadhyay, S
Sasson, Y
机构：
[1] Hebrew Univ Jerusalem, Casali Inst Appl Chem, IL-91904 Jerusalem, Israel
[2] Univ Calif Berkeley, Dept Chem Engn, Berkeley, CA 94720 USA
来源：
TETRAHEDRON LETTERS | 2005年 / 46卷 / 11期
关键词：
knoevenagel condensation; Pd/C; ionic liquids; hydrogenation;
D O I：
10.1016/j.tetlet.2005.01.092
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A domino reaction composed of a Knoevenagel condensation combined with a simultaneous catalytic hydrogenation is reported in an ionic liquid solvent under mild conditions (298-363 K and 300 kPa). No interference between the catalysts (Pd/C and amine acetate salt) of the two diverse steps was monitored. The product could be neatly extracted by diethyl ether and the solvent containing the catalysts could be recycled and reused five times without any loss in activity or selectivity. The same methodology in a common organic solvent such as DMA resulted in significant competing parallel hydrogenation of the aidehyde to alcohol. (C) 2005 Elsevier Ltd. All rights reserved.
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收藏
页码：1885 / 1887
页数：3
相关论文
共 19 条
  • [1] Unexpected side reactions of imidazolium-based ionic liquids in the base-catalysed Baylis-Hillman reaction
    Aggarwal, VK
    Emme, I
    Mereu, A
    [J]. CHEMICAL COMMUNICATIONS, 2002, (15) : 1612 - 1613
  • [2] Ionic liquid-phase asymmetric catalytic hydrogenation: hydrogen concentration effects on enantioselectivity
    Berger, A
    de Souza, RF
    Delgado, MR
    Dupont, J
    [J]. TETRAHEDRON-ASYMMETRY, 2001, 12 (13) : 1825 - 1828
  • [3] Asymmetric hydrogenation and catalyst recycling using ionic liquid and supercritical carbon dioxide
    Brown, RA
    Pollet, P
    McKoon, E
    Eckert, CA
    Liotta, CL
    Jessop, PG
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (06) : 1254 - 1255
  • [4] Ce S., 2003, SYNTHESIS-STUTTGART, P555
  • [5] Chauvin Y, 1995, ANGEW CHEM INT EDIT, V34, P2698
  • [6] A novel system consisting of Rh-DuPHOS and ionic liquid for asymmetric hydrogenations
    Guernik, S
    Wolfson, A
    Herskowitz, M
    Greenspoon, N
    Geresh, S
    [J]. CHEMICAL COMMUNICATIONS, 2001, (22) : 2314 - 2315
  • [7] Heterogeneous Heck reaction catalyzed by Pd/C in ionic liquid
    Hagiwara, H
    Shimizu, Y
    Hoshi, T
    Suzuki, T
    Ando, M
    Ohkubo, K
    Yokoyama, C
    [J]. TETRAHEDRON LETTERS, 2001, 42 (26) : 4349 - 4351
  • [8] HO TL, 1993, ANGEW CHEM INT EDIT, V32, P131
  • [9] Hydrogenation of olefins using ligand-stabilized palladium nanoparticles in an ionic liquid
    Huang, J
    Jiang, T
    Han, BX
    Gao, HX
    Chang, YH
    Zhao, GY
    Wu, WZ
    [J]. CHEMICAL COMMUNICATIONS, 2003, (14) : 1654 - 1655
  • [10] Jones G., 1967, ORGANICREACTIONS, V15, P204, DOI [DOI 10.1002/0471264180.OR015.02, 10.1002/0471264180.or015.02]
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