Halide inhibition of the copper-catalysed azide-alkyne cycloaddition

被引：14
作者：
Moorman, Rebekah M. [1 ]
Collier, Matthew B. [1 ]
Frohock, Bram H. [1 ]
Womble, Michael D. [1 ]
Chalker, Justin M. [1 ]
机构：
[1] Univ Tulsa, Dept Chem & Biochem, Tulsa, OK 74104 USA
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2015年 / 13卷 / 07期
关键词：
CLICK CHEMISTRY; 1,4-DISUBSTITUTED 1,2,3-TRIAZOLES;
D O I：
10.1039/c4ob02479f
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Chloride, bromide and iodide are inhibitors of the copper-catalysed azide-alkyne cycloaddition, with iodide exhibiting the most detrimental effects on rates and yields. A study of this inhibition is presented, along with experimental protocols to accommodate the presence of halides in this widely used reaction.
引用
收藏
页码：1974 / 1978
页数：5
相关论文
共 31 条
  • [1] Advancements in the mechanistic understanding of the copper-catalyzed azide-alkyne cycloaddition
    Berg, Regina
    Straub, Bernd F.
    [J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 : 2715 - 2750
  • [2] Click Chemistry and Bioorthogonal Reactions: Unprecedented Selectivity in the Labeling of Biological Molecules
    Best, Michael D.
    [J]. BIOCHEMISTRY, 2009, 48 (28) : 6571 - 6584
  • [3] CuI-catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective
    Bock, VD
    Hiemstra, H
    van Maarseveen, JH
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (01) : 51 - 68
  • [4] Polytriazoles as copper(I)-stabilizing ligands in catalysis
    Chan, TR
    Hilgraf, R
    Sharpless, KB
    Fokin, VV
    [J]. ORGANIC LETTERS, 2004, 6 (17) : 2853 - 2855
  • [5] Fagnou K, 2002, ANGEW CHEM INT EDIT, V41, P26, DOI 10.1002/1521-3773(20020104)41:1<26::AID-ANIE26>3.0.CO
  • [6] 2-9
  • [7] Combination of perfluoroalkyl and triazole moieties:: A new recovery strategy for TEMPO
    Gheorghe, Alexandru
    Chinnusamy, Tarnilselvi
    Cuevas-Yanez, Erick
    Hilgers, Petra
    Reiser, Oliver
    [J]. ORGANIC LETTERS, 2008, 10 (19) : 4171 - 4174
  • [8] Click chemistry, a powerful tool for pharmaceutical sciences
    Hein, Christopher D.
    Liu, Xin-Ming
    Wang, Dong
    [J]. PHARMACEUTICAL RESEARCH, 2008, 25 (10) : 2216 - 2230
  • [9] Labeling Live Cells by Copper-Catalyzed Alkyne-Azide Click Chemistry
    Hong, Vu
    Steinmetz, Nicole F.
    Manchester, Marianne
    Finn, M. G.
    [J]. BIOCONJUGATE CHEMISTRY, 2010, 21 (10) : 1912 - 1916
  • [10] Analysis and Optimization of Copper-Catalyzed Azide-Alkyne Cycloaddition for Bioconjugation
    Hong, Vu
    Presolski, Stanislav I.
    Ma, Celia
    Finn, M. G.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) : 9879 - 9883
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