A new water-soluble ligand for efficient copper-catalyzed Huisgen cycloaddition of aliphatic azides and alkynes

被引:21
作者
Szafranski, Przemyslaw W. [1 ]
Kasza, Patryk [1 ,2 ]
Cegla, Marek T. [1 ]
机构
[1] Jagiellonian Univ, Fac Pharm, Dept Organ Chem, Coll Med, PL-30688 Krakow, Poland
[2] Jagiellonian Univ, Fac Chem, Dept Organ Chem, PL-30060 Krakow, Poland
关键词
Cycloaddition; Azides; Alkynes; Copper; Heterocycles; CLICK-CHEMISTRY; 1,3-DIPOLAR CYCLOADDITIONS; POLYMER;
D O I
10.1016/j.tetlet.2015.09.110
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Efficient procedures for the copper-catalyzed Huisgen cycloaddition reaction in aqueous media were developed using a novel water-soluble catalytic ligand, 2-{4-[(dimethylamino)methyl]-1,2,3-triazol-1-yl)cyclohexan-1-ol (AMTC). A series of aliphatic and aromatic substrates were tested and compared to the well-known tris(triazole)amine ligands (TBTA and THPTA). The effect of solvent composition was also investigated. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6244 / 6247
页数:4
相关论文
共 32 条
[1]  
[Anonymous], 2014, LOGP VAL WER CALC US
[2]   'Click' chemistry in polymer and material science: An update [J].
Binder, Wolfgang H. ;
Sachsenhofer, Robert .
MACROMOLECULAR RAPID COMMUNICATIONS, 2008, 29 (12-13) :952-981
[3]   'Click' chemistry in polymer and materials science [J].
Binder, Wolfgang H. ;
Sachsenhofer, Robert .
MACROMOLECULAR RAPID COMMUNICATIONS, 2007, 28 (01) :15-54
[4]   CuI-catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective [J].
Bock, VD ;
Hiemstra, H ;
van Maarseveen, JH .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (01) :51-68
[5]   Synthesis and evaluation of the quorum sensing inhibitory effect of substituted triazolyldihydrofuranones [J].
Brackman, Gilles ;
Risseeuw, Martijn ;
Celen, Shari ;
Cos, Paul ;
Maes, Louis ;
Nelis, Hans J. ;
Van Calenbergh, Serge ;
Coenye, Tom .
BIOORGANIC & MEDICINAL CHEMISTRY, 2012, 20 (15) :4737-4743
[6]   Polytriazoles as copper(I)-stabilizing ligands in catalysis [J].
Chan, TR ;
Hilgraf, R ;
Sharpless, KB ;
Fokin, VV .
ORGANIC LETTERS, 2004, 6 (17) :2853-2855
[7]   Organic Synthesis "On Water" [J].
Chanda, Arani ;
Fokin, Valery V. .
CHEMICAL REVIEWS, 2009, 109 (02) :725-748
[8]   New mono- and bidentate P-ligands using one-pot click-chemistry: synthesis and application in Rh-catalyzed hydroformylation [J].
Dubrovina, Natalia V. ;
Domke, Lutz ;
Shuklov, Ivan A. ;
Spannenberg, Anke ;
Franke, Robert ;
Villinger, Alexander ;
Boerner, Armin .
TETRAHEDRON, 2013, 69 (41) :8809-8817
[9]   2-Ethynylpyridine-Promoted Rapid Copper(I) Chloride Catalyzed Azide-Alkyne Cycloaddition Reaction in Water [J].
Hiroki, Hidekatsu ;
Ogata, Kenichi ;
Fukuzawa, Shin-ichi .
SYNLETT, 2013, 24 (07) :843-846
[10]   Analysis and Optimization of Copper-Catalyzed Azide-Alkyne Cycloaddition for Bioconjugation [J].
Hong, Vu ;
Presolski, Stanislav I. ;
Ma, Celia ;
Finn, M. G. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9879-9883