Ionic liquids vs. microporous solids as reusable reaction media for the catalytic C-H functionalization of indoles with alcohols

被引:25
作者
Cirujano, Francisco G. [1 ]
Stalpaert, Maxime [1 ]
De Vos, Dirk E. [1 ]
机构
[1] Univ Leuven, KU Leuven, Dept Microbial & Mol Syst, Ctr Surface Chem & Catalysis,Leuven Chem&Tech, Celestijnenlaan 200F,Post Box 2461, B-3001 Heverlee, Belgium
基金
欧盟地平线“2020”;
关键词
FRIEDEL-CRAFTS ALKYLATION; METAL-ORGANIC FRAMEWORKS; PERFORMANCE; MOFS; BEHAVIOR; PATHWAY; ACIDS; FE;
D O I
10.1039/c8gc00738a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
High performance reusable catalysts and reaction media are evaluated for the green alkylation of indoles with alcohols under mild and solvent-free conditions. For a range of Bronsted and Lewis acid catalytic sites in different environments, such as inexpensive ionic liquids or microporous solids, we show a correlation between the acid strength and catalytic activity, achieving the highest turnovers reported for strong acid sites upon five reuses under mild conditions.
引用
收藏
页码:2481 / 2485
页数:5
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共 46 条
  • [1] Deep Eutectic Solvents: The Organic Reaction Medium of the Century
    Alonso, Diego A.
    Baeza, Alejandro
    Chinchilla, Rafael
    Guillena, Gabriela
    Pastor, Isidro M.
    Ramon, Diego J.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (04) : 612 - 632
  • [2] THE DIELECTRIC CONSTANTS, POLARIZATIONS AND DIPOLE MOMENTS OF SOME ALKYLBENZENES
    ALTSHULLER, AP
    [J]. JOURNAL OF PHYSICAL CHEMISTRY, 1954, 58 (05) : 392 - 395
  • [3] Applying green processes and techniques to simplify reaction work-ups
    Andrade, Carlos Kleber Z.
    Dar, Abdul Rouf
    [J]. TETRAHEDRON, 2016, 72 (47) : 7375 - 7391
  • [4] MESOPOROUS ALUMINOSILICATE MCM-41 AS A CONVENIENT ACID CATALYST FOR FRIEDEL-CRAFTS ALKYLATION OF A BULKY AROMATIC COMPOUND WITH CINNAMYL ALCOHOL
    ARMENGOL, E
    CANO, ML
    CORMA, A
    GARCIA, H
    NAVARRO, MT
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (05) : 519 - 520
  • [5] THE H3O+ CATION IN AROMATIC SOLVENTS - SYNTHESIS, STRUCTURE, AND SOLUTION BEHAVIOR OF [H3O+.18-CROWN-6][CL-H-CL]
    ATWOOD, JL
    BOTT, SG
    COLEMAN, AW
    ROBINSON, KD
    WHETSTONE, SB
    MEANS, CM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (26) : 8100 - 8101
  • [6] Pathway to Vinyl Chloride Production via Dehydrochlorination of 1,2-Dichloroethane in Ionic Liquid Media
    Boudewijns, Tom
    Piccinini, Marco
    Degraeve, Paul
    Liebens, Armin
    De Vos, Dirk
    [J]. ACS CATALYSIS, 2015, 5 (07): : 4043 - 4047
  • [7] The Growing Impact of Catalysis in the Pharmaceutical Industry
    Busacca, Carl A.
    Fandrick, Daniel R.
    Song, Jinhua J.
    Senanayake, Chris H.
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (11-12) : 1825 - 1864
  • [8] Cobalt-catalysed reductive C-H alkylation of indoles using carboxylic acids and molecular hydrogen
    Cabrero-Antonino, Jose R.
    Adam, Rosa
    Junge, Kathrin
    Beller, Matthias
    [J]. CHEMICAL SCIENCE, 2017, 8 (09) : 6439 - 6450
  • [9] Environmentally friendly and regioselective C3-alkylation of indoles with alcohols through a hydrogen autotransfer strategy
    Cano, Rafael
    Yus, Miguel
    Ramon, Diego J.
    [J]. TETRAHEDRON LETTERS, 2013, 54 (26) : 3394 - 3397
  • [10] A facile synthesis of alkylated nitrogen heterocycles catalysed by 3D mesoporous aluminosilicates with cage type pores in aqueous medium
    Chakravarti, Rajashree
    Kalita, Pranjal
    Selvan, S. Tamil
    Oveisi, Hamid
    Balasubramanian, V. V.
    Kantam, M. Lakshmi
    Vinu, Ajayan
    [J]. GREEN CHEMISTRY, 2010, 12 (01) : 49 - 53