When CuAAC 'Click Chemistry' goes heterogeneous

被引:150
作者
Chassaing, S. [1 ]
Beneteau, V. [2 ]
Pale, P. [2 ]
机构
[1] Univ Toulouse, Inst Technol Avancees Sci Vivant, Toulouse, France
[2] Univ Strasbourg, Inst Chim Strasbourg, UMR 7177, 4 Rue B Pascal, F-67000 Strasbourg, France
关键词
AZIDE-ALKYNE CYCLOADDITION; ONE-POT SYNTHESIS; COPPER-CATALYZED HUISGEN; METAL-ORGANIC FRAMEWORK; NANOSILICA TRIAZINE DENDRIMER; CU-II-HYDROTALCITE; 1,3-DIPOLAR CYCLOADDITION; 1,4-DISUBSTITUTED 1,2,3-TRIAZOLES; REUSABLE CATALYST; TERMINAL ALKYNES;
D O I
10.1039/c5cy01847a
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
Within the green chemistry context, heterogeneous catalysis applied to organic synthesis is becoming an increasingly important field, bringing its own innovation and specific properties to organic chemistry. The well known 'click chemistry' is now challenged by this paradigm change and numerous methods involving heterogeneously catalyzed click chemistry have been and are currently being developed. This review covers these developments and shows that various reliable heterogeneous methods, alternative to the commonly used Meldal-Sharpless method, do exist for click chemistry, including those involving flow chemistry, and that they could be applied to a variety of compounds, solving some problems faced by more conventional methods.
引用
收藏
页码:923 / 957
页数:35
相关论文
共 277 条
  • [1] New routes to Cu(I)/Cu nanocatalysts for the multicomponent click synthesis of 1,2,3-triazoles
    Abdulkin, Pavel
    Moglie, Yanina
    Knappett, Benjamin R.
    Jefferson, David A.
    Yus, Miguel
    Alonso, Francisco
    Wheatley, Andrew E. H.
    [J]. NANOSCALE, 2013, 5 (01) : 342 - 350
  • [2] Click Chemistry: 1,2,3-Triazoles as Pharmacophores
    Agalave, Sandip G.
    Maujan, Suleman R.
    Pore, Vandana S.
    [J]. CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (10) : 2696 - 2718
  • [3] Enhanced reactivity of dinuclear Copper(I) acetylides in dipolar cycloadditions
    Ahlquist, Marten
    Fokin, Valery V.
    [J]. ORGANOMETALLICS, 2007, 26 (18) : 4389 - 4391
  • [4] Polymer-Supported Azide and Copper(I): Green Reusable Reagent and Catalyst for Click Cyclization
    Albadi, Jalal
    Keshavarz, Mosadegh
    [J]. SYNTHETIC COMMUNICATIONS, 2013, 43 (15) : 2019 - 2030
  • [5] Copper iodide nanoparticles on poly(4-vinyl pyridine): A new and efficient catalyst for multicomponent click synthesis of 1,4-disubstituted-1,2,3-triazoles in water
    Albadi, Jalal
    Keshavarz, Mosadegh
    Shirini, Farhad
    Vafaie-nezhad, Masoumeh
    [J]. CATALYSIS COMMUNICATIONS, 2012, 27 : 17 - 20
  • [6] Alberico F., 2000, SOLID PHASE SYNTHESI
  • [7] 'Click chemistry' in CuI-zeolites:: a convenient access to glycoconjugates
    Alix, Aurlien
    Chassaing, Stefan
    Pale, Patrick
    Sommer, Jean
    [J]. TETRAHEDRON, 2008, 64 (37) : 8922 - 8929
  • [8] Honeycomb Carbon: A Review of Graphene
    Allen, Matthew J.
    Tung, Vincent C.
    Kaner, Richard B.
    [J]. CHEMICAL REVIEWS, 2010, 110 (01) : 132 - 145
  • [9] Alkenes as Azido Precursors for the One-Pot Synthesis of 1,2,3-Triazoles Catalyzed by Copper Nanoparticles on Activated Carbon
    Alonso, Francisco
    Moglie, Yanina
    Radivoy, Gabriel
    Yus, Miguel
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (10) : 5031 - 5037
  • [10] Copper-Catalysed Multicomponent Click Synthesis of 5-Alkynyl 1,2,3-Triazoles under Ambient Conditions
    Alonso, Francisco
    Moglie, Yanina
    Radivoy, Gabriel
    Yus, Miguel
    [J]. SYNLETT, 2012, (15) : 2179 - 2182