Copper(I)-Catalyzed Azide-Alkyne Cycloadditions in Ionic Liquids under Amine-Free Conditions

被引:14
|
作者
Vecchi, Alessandra [1 ]
Chambery, Angela [2 ]
Chiappe, Cinzia [3 ]
Marra, Alberto [1 ]
Dondoni, Alessandro [1 ]
机构
[1] Univ Ferrara, Dipartmento Chim, Chim Organ Lab, I-44100 Ferrara, Italy
[2] Univ Naples 2, Dipartimento Sci Vita, I-81100 Caserta, Italy
[3] Univ Pisa, Dipartimento Chim & Chim Ind, I-56126 Pisa, Italy
来源
SYNTHESIS-STUTTGART | 2010年 / 12期
关键词
alkynes; azides; carbohydrates; copper; cycloadditions; CARBOHYDRATE-CHEMISTRY; CLICK CHEMISTRY; ADAMANTANE; REACTIVITY; SOLVENTS; GREEN;
D O I
10.1055/s-0029-1218760
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Copper(I) iodide catalyzed cycloadditions of various combinations of structurally diverse organic azides and terminal alkynes were carried out in a commercially available, polyoxygenated ionic liquid (AMMOENG 100 (TM)) without addition of free amine. Unlike the previously tested ionic liquids, this solvent led exclusively to the 1,4-disubstituted triazole regioisomer.
引用
收藏
页码:2043 / 2048
页数:6
相关论文
共 50 条
  • [1] Asymmetric Copper-Catalyzed Azide-Alkyne Cycloadditions
    Brittain, William D. G.
    Buckley, Benjamin R.
    Fossey, John S.
    ACS CATALYSIS, 2016, 6 (06): : 3629 - 3636
  • [2] Mechanistic Insights into Copper(I)-Catalyzed Azide-Alkyne Cycloadditions using Continuous Flow Conditions
    Fuchs, Michael
    Goessler, Walter
    Pilger, Christian
    Kappe, C. Oliver
    ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (2-3) : 323 - 328
  • [3] Green Methodologies for Copper(I)-Catalyzed Azide-Alkyne Cycloadditions: A Comparative Study
    Trujillo, Marissa
    Hull-Crew, Clayton
    Outlaw, Andrew
    Stewart, Kevin
    Taylor, Loren
    George, Laura
    Duensing, Allison
    Tracey, Breanna
    Schoffstall, Allen
    MOLECULES, 2019, 24 (05)
  • [4] Peptidomimetics via copper-catalyzed azide-alkyne cycloadditions
    Angell, Yu L.
    Burgess, Kevin
    CHEMICAL SOCIETY REVIEWS, 2007, 36 (10) : 1674 - 1689
  • [5] Structural Determinants of Alkyne Reactivity in Copper-Catalyzed Azide-Alkyne Cycloadditions
    Zhang, Xiaoguang
    Liu, Peiye
    Zhu, Lei
    MOLECULES, 2016, 21 (12)
  • [6] Direct Evidence of a Dinuclear Copper Intermediate in Cu(I)-Catalyzed Azide-Alkyne Cycloadditions
    Worrell, B. T.
    Malik, J. A.
    Fokin, V. V.
    SCIENCE, 2013, 340 (6131) : 457 - 460
  • [7] Chalcones and Chromones in Copper-catalyzed Azide-Alkyne Cycloadditions (CuAAC)
    Tome, Sara M.
    Tome, Augusto C.
    Soengas, Raquel G.
    Silva, Artur M. S.
    CURRENT ORGANIC CHEMISTRY, 2018, 22 (13) : 1307 - 1325
  • [8] On the Mechanism of Copper(I)-Catalyzed Azide-Alkyne Cycloaddition
    Zhu, Lei
    Brassard, Christopher J.
    Zhang, Xiaoguang
    Guha, P. M.
    Clark, Ronald J.
    CHEMICAL RECORD, 2016, 16 (03): : 1501 - 1517
  • [9] Copper-free azide-alkyne cycloadditions: New insights and perspectives
    Lutz, Jean-Francois
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (12) : 2182 - 2184
  • [10] A one carbon staple for orthogonal copper-catalyzed azide-alkyne cycloadditions
    Wright, Karen
    Quinodoz, Pierre
    Drouillat, Bruno
    Couty, Francois
    CHEMICAL COMMUNICATIONS, 2017, 53 (02) : 321 - 323