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
  • [31] Dicopper Cu(I)Cu(I) and Cu(I)Cu(II) Complexes in Copper-Catalyzed Azide-Alkyne Cycloaddition
    Ziegler, Micah S.
    Lakshmi, K. V.
    Tilley, T. Don
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (15) : 5378 - 5386
  • [32] Development and Applications of the Copper-Catalyzed Azide-Alkyne Cycloaddition (CuAAC) as a Bioorthogonal Reaction
    Li, Li
    Zhang, Zhiyuan
    MOLECULES, 2016, 21 (10)
  • [33] Star polymers by photoinduced copper-catalyzed azide-alkyne cycloaddition click chemistry
    Tinmaz, Hatice Busra
    Arslan, Irem
    Tasdelen, Mehmet Atilla
    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2015, 53 (14) : 1687 - 1695
  • [34] Postsynthetic DNA Modification through the Copper-Catalyzed Azide-Alkyne Cycloaddition Reaction
    Gramlich, Philipp M. E.
    Wirges, Christian T.
    Manetto, Antonio
    Carell, Thomas
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (44) : 8350 - 8358
  • [35] Photoinduced Vesicle Formation via the Copper-Catalyzed Azide-Alkyne Cycloaddition Reaction
    Konetski, Danielle
    Gong, Tao
    Bowman, Christopher N.
    LANGMUIR, 2016, 32 (32) : 8195 - 8201
  • [36] The mechanism of copper-catalyzed azide-alkyne cycloaddition reaction: A quantum mechanical investigation
    Ozen, Cihan
    Tuzun, Nurcan S.
    JOURNAL OF MOLECULAR GRAPHICS & MODELLING, 2012, 34 : 101 - 107
  • [37] 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
  • [38] An efficient and recyclable thiourea-supported copper(I) chloride catalyst for azide-alkyne cycloaddition reactions
    Barman, Milan Kr.
    Sinha, Ashish Kumar
    Nembenna, Sharanappa
    GREEN CHEMISTRY, 2016, 18 (08) : 2534 - 2541
  • [39] Azide-Alkyne Cycloaddition (CuAAC) in Alkane Solvents Catalyzed by Fluorinated NHC Copper(I) Complex
    Topchiy, Maxim A.
    Ageshina, Alexandra A.
    Gribanov, Pavel S.
    Masoud, Salekh M.
    Akmalov, Timur R.
    Nefedov, Sergey E.
    Osipov, Sergey N.
    Nechaev, Mikhail S.
    Asachenko, Andrey F.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (05) : 1016 - 1020
  • [40] Beyond copper-catalyzed azide-alkyne 1,3-dipolar cycloaddition: Synthesis and mechanism insights
    Gomes, Roberto S.
    Jardim, Guilherme A. M.
    de Carvalho, Renato L.
    Araujo, Maria H.
    da Silva Junior, Eufranio N.
    TETRAHEDRON, 2019, 75 (27) : 3697 - 3712