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
  • [41] Rhodium(I)-Catalyzed Azide-Alkyne Cycloaddition (RhAAC) of Internal Alkynylphosphonates with High Regioselectivities under Mild Conditions
    Song, Wangze
    Zheng, Nan
    Li, Ming
    Ullah, Karim
    Zheng, Yubin
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (13) : 2429 - 2434
  • [42] Lignocellulosic Micro- and Nanomaterials as Copper Frames for the Evaluation of the Copper(I)-Catalyzed Azide-Alkyne Cycloaddition
    Owens, Charles W.
    Oporto, Gloria S.
    Soderberg, Bjorn C. G.
    Lambson, Katherine E.
    JOURNAL OF NANOMATERIALS, 2017, 2017
  • [43] Copper-catalyzed azide-alkyne cycloaddition (CuAAC) and beyond: new reactivity of copper(I) acetylides
    Hein, Jason E.
    Fokin, Valery V.
    CHEMICAL SOCIETY REVIEWS, 2010, 39 (04) : 1302 - 1315
  • [44] Improved Metal-Adhesive Polymers from Copper(I)-Catalyzed Azide-Alkyne Cycloaddition
    Accurso, Adrian A.
    Delaney, Mac
    O'Brien, Jeff
    Kim, Hyonny
    Iovine, Peter M.
    Diaz Diaz, David
    Finn, M. G.
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (34) : 10710 - 10719
  • [45] Photoinitiated copper(I) catalyzed azide-alkyne cycloaddition (CuAAC) reaction for conductive network synthesis
    El-Zaatari, Bassil
    Tibbits, Andrew
    Kloxin, Christopher
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 255
  • [46] Compatibility between the cysteine-cyclopentenedione reaction and the copper(I)-catalyzed azide-alkyne cycloaddition
    Agramunt, Jordi
    Saltor, Laia
    Pedroso, Enrique
    Grandas, Anna
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (47) : 9185 - 9190
  • [47] Photopolymerization Reactions Using the Photoinitiated Copper (I)-Catalyzed Azide-Alkyne Cycloaddition (CuAAC) Reaction
    Gong, Tao
    Adzima, Brian J.
    Baker, Noah H.
    Bowman, Christopher N.
    ADVANCED MATERIALS, 2013, 25 (14) : 2024 - 2028
  • [48] Synthesis of DNA Modified with Boronic Acid: Compatibility to Copper(I)-Catalyzed Azide-Alkyne Cycloaddition
    Steinmeyer, Jeannine
    Wagenknechte, Hans-Achim
    BIOCONJUGATE CHEMISTRY, 2018, 29 (02) : 431 - 436
  • [49] Peptide cyclodimerization by copper-catalyzed azide-alkyne cycloaddition.
    Punna, S
    Kuzelka, J
    Wang, Q
    Finn, MG
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U387 - U387
  • [50] Autocatalytic Cycles in a Copper-Catalyzed Azide-Alkyne Cycloaddition Reaction
    Semenov, Sergey N.
    Belding, Lee
    Cafferty, Brian J.
    Mousavi, Maral P. S.
    Finogenova, Anastasiia M.
    Cruz, Ricardo S.
    Skorb, Ekaterina V.
    Whitesides, George M.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (32) : 10221 - 10232
12345