C-3 alkylation of oxindole with alcohols catalyzed by an indene-functionalized mesoporous iridium catalyst

被引:17
作者
Liu, Guohua [1 ]
Huang, Tianzeng [1 ]
Zhang, Yuli [1 ]
Liang, Xiaohui [1 ]
Li, Yunsheng [1 ]
Li, Hexing [1 ]
机构
[1] Shanghai Normal Univ, Minist Educ, Key Lab Resource Chem, Shanghai 200234, Peoples R China
关键词
Heterogeneous catalyst; Iridium; Alkylation; Mesoporous materials; DIRECT ALPHA-ALKYLATION; ASYMMETRIC CATALYSIS; KETONES; ISOMERIZATION; COMPLEX; DESIGN;
D O I
10.1016/j.catcom.2010.12.021
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
A heterogeneous indene-based iridium catalyst with a highly ordered dimensional-hexagonal mesostructure was prepared through complexation of IrCI(3) with the indene-functionalized SBA-15 silica materials. During C-3 alkylation of oxindole with various alcohols, this heterogeneous catalyst exhibited highly catalytic activity (up to 93%). Such a catalyst could be recovered easily and used repetitively eight times without significantly affecting its catalytic activity. (C) 2010 Elsevier B.V. All rights reserved.
引用
收藏
页码:655 / 659
页数:5
相关论文
共 33 条
  • [1] Alcohols for the α-Alkylation of Methyl Ketones and Indirect Aza-Wittig Reaction Promoted by Nickel Nanoparticles
    Alonso, Francisco
    Riente, Paola
    Yus, Miguel
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (29) : 4908 - 4914
  • [2] Asymmetric catalysis on solids
    Bein, T
    [J]. CURRENT OPINION IN SOLID STATE & MATERIALS SCIENCE, 1999, 4 (01) : 85 - 96
  • [3] Functionalized monolayers on ordered mesoporous supports
    Feng, X
    Fryxell, GE
    Wang, LQ
    Kim, AY
    Liu, J
    Kemner, KM
    [J]. SCIENCE, 1997, 276 (5314) : 923 - 926
  • [4] Design, synthesis, and SAR of new pyrrole-oxindole progesterone receptor modulators leading to 5-(7-Fluoro-3,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-5-yl)-1-methyl-1H-pyrrole-2-carbonitrile (WAY-255348)
    Fensome, Andrew
    Adams, William R.
    Adams, Andrea L.
    Berrodin, Tom J.
    Cohen, Jeff
    Huselton, Christine
    Illenberger, Arthur
    Kern, Jeffrey C.
    Hudak, Valerie A.
    Marella, Michael A.
    Melenski, Edward G.
    McComas, Casey C.
    Mugford, Cheryl A.
    Slayden, Ov D.
    Yudt, Matthew
    Zhang, Zhiming
    Zhang, Puwen
    Zhu, Yuan
    Winneker, Richard C.
    Wrobel, Jay E.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (06) : 1861 - 1873
  • [5] Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents
    Galliford, Chris V.
    Scheidt, Karl A.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (46) : 8748 - 8758
  • [6] Iridium catalysed C-3 alkylation of oxindole with alcohols under solvent free thermal or microwave conditions
    Grigg, Ronald
    Whitney, Simon
    Sridharan, Visuvanathar
    Keep, Ann
    Derrick, Andrew
    [J]. TETRAHEDRON, 2009, 65 (22) : 4375 - 4383
  • [7] Asymmetric heterogeneous catalysis
    Heitbaum, Maja
    Glorius, Frank
    Escher, Iris
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (29) : 4732 - 4762
  • [8] Non-covalently solid-phase bound catalysts for organic synthesis
    Horn, J
    Michalek, F
    Tzschucke, CC
    Bannwarth, W
    [J]. IMMOBILIZED CATALYSTS: SOLID PHASES, IMMOBILIZATION AND APPLICATIONS, 2004, 242 : 43 - 75
  • [9] Ruthenium-Catalyzed Alkylation of Oxindole with Alcohols
    Jensen, Thomas
    Madsen, Robert
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (10) : 3990 - 3992
  • [10] Paratunamides A-D, oxindole alkaloids from Cinnamodendron axillare
    Kagata, Toshinori
    Saito, Shizuka
    Shigemori, Hideyuki
    Ohsaki, Ayumi
    Ishiyama, Haruaki
    Kubota, Takaaki
    Kobayashi, Jun'ichi
    [J]. JOURNAL OF NATURAL PRODUCTS, 2006, 69 (10): : 1517 - 1521