Copper(I) Acetate: A Structurally Simple but Highly Efficient Dinuclear Catalyst for Copper-Catalyzed Azide-Alkyne Cycloaddition

被引:101
|
作者
Shao, Changwei [1 ]
Cheng, Guolin [1 ]
Su, Deyong [1 ]
Xu, Jimin [1 ]
Wang, Xinyan [1 ]
Hu, Yuefei [1 ]
机构
[1] Tsinghua Univ, Dept Chem, Minist Educ, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Beijing 100084, Peoples R China
关键词
acetylides; catalysts; click chemistry; copper; cycloaddition; 1,3-DIPOLAR CYCLOADDITION; CRYSTAL-STRUCTURE; CLICK CHEMISTRY; HETEROGENEOUS CATALYST; TERMINAL ALKYNES; POLYMERS; LIGANDS; CYCLIZATION; DENDRIMERS; COMPLEX;
D O I
10.1002/adsc.200900768
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
In this article, the structurally well-defined dinuclear complex copper(I) acetate was studied in detail and was developed as a highly practical and efficient catalyst for the copper(I)-catalyzed azide-alkyne cycloaddition. The "bare" phenylethynylcopper(I) (i.e., with no exogeneous ligands) was isolated as an intermediate, which can be converted into an active catalytic species by treatment with acetic acid (in situ produced in the reaction) to efficiently catalyze the azide-alkyne cycloaddition under mild conditions.
引用
收藏
页码:1587 / 1592
页数:6
相关论文
共 50 条
  • [21] Asymmetric Copper-Catalyzed Azide-Alkyne Cycloadditions
    Brittain, William D. G.
    Buckley, Benjamin R.
    Fossey, John S.
    ACS CATALYSIS, 2016, 6 (06): : 3629 - 3636
  • [22] Copper(I) oxide and benzoic acid 'on water': a highly practical and efficient catalytic system for copper(I)-catalyzed azide-alkyne cycloaddition
    Shao, Changwei
    Zhu, Rui
    Luo, Sheng
    Zhang, Qun
    Wang, Xinyan
    Hu, Yuefei
    TETRAHEDRON LETTERS, 2011, 52 (29) : 3782 - 3785
  • [23] Asymmetric Copper(I)-Catalyzed Azide-Alkyne Cycloaddition to Quaternary Oxindoles
    Zhou, Feng
    Tan, Chen
    Tang, Jing
    Zhang, Yan-Yan
    Gao, Wei-Ming
    Wu, Hai-Hong
    Yu, Yi-Hua
    Zhou, Jian
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (30) : 10994 - 10997
  • [24] Alkyne-azide cycloaddition catalyzed by a dinuclear copper(I) complex
    Chen, Hong-Bin
    Abeyrathna, Nawodi
    Liao, Yi
    TETRAHEDRON LETTERS, 2014, 55 (48) : 6575 - 6576
  • [25] Dinuclear Copper Intermediates in Copper(I)-Catalyzed Azide-Alkyne Cycloaddition Directly Observed by Electrospray Ionization Mass Spectrometry
    Iacobucci, Claudio
    Reale, Samantha
    Gal, Jean-Francois
    De Angelis, Francesco
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (10) : 3065 - 3068
  • [26] Copper on Iron: Catalyst and Scavenger for Azide-Alkyne Cycloaddition
    Kovacs, Szabolcs
    Zih-Perenyi, Katalin
    Revesz, Adam
    Novak, Zoltan
    SYNTHESIS-STUTTGART, 2012, 44 (24): : 3722 - 3730
  • [27] Apparent copper(II) catalyzed azide-alkyne cycloaddition
    Brotherton, Wendy S.
    Zhu, Lei
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
  • [28] Development and Applications of the Copper-Catalyzed Azide-Alkyne Cycloaddition (CuAAC) as a Bioorthogonal Reaction
    Li, Li
    Zhang, Zhiyuan
    MOLECULES, 2016, 21 (10)
  • [29] Azidoperfluoroalkanes: Synthesis and Application in Copper(I)-Catalyzed Azide-Alkyne Cycloaddition
    Blastik, Zsofia E.
    Voltrova, Svatava
    Matousek, Vaclav
    Jurasek, Bronislav
    Manley, David W.
    Klepetarova, Blanka
    Beier, Petr
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (01) : 346 - 349
  • [30] Photoinduced Vesicle Formation via the Copper-Catalyzed Azide-Alkyne Cycloaddition Reaction
    Konetski, Danielle
    Gong, Tao
    Bowman, Christopher N.
    LANGMUIR, 2016, 32 (32) : 8195 - 8201