Aqueous 1,3-dipolar cycloadditions promoted by copper nanoparticles in polydiacetylene micelles

被引:41
作者
Clarisse, Damien [1 ]
Prakash, Praveen [1 ]
Geertsen, Valerie [2 ]
Miserque, Frederic [3 ]
Gravel, Edmond [1 ]
Doris, Eric [1 ]
机构
[1] Univ Paris Saclay, SCBM, CEA, F-91191 Gif Sur Yvette, France
[2] Univ Paris Saclay, CNRS, NIMBE, CEA, F-91191 Gif Sur Yvette, France
[3] Univ Paris Saclay, Serv Etud Corros & Comportement Mat Environm SCCM, CEA, F-91191 Gif Sur Yvette, France
关键词
AZIDE-ALKYNE CYCLOADDITION; CLICK CHEMISTRY; TERMINAL ALKYNES; HETEROGENEOUS CATALYSIS; DRUG-DELIVERY; NANOCRYSTALS; WATER;
D O I
10.1039/c7gc01017f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel colloidal catalyst was developed through the encapsulation of cuprous oxide nanoparticles in polydiacetylene micelles. The Cu-based catalyst was applied to the Huisgen cycloaddition reaction in fully aqueous medium. The process neither requires heating nor a controlled atmosphere and the catalyst can be recycled in subsequent reactions without any loss of activity.
引用
收藏
页码:3112 / 3115
页数:4
相关论文
共 31 条
[1]   Copper nanoparticles in click chemistry: an alternative catalytic system for the cycloaddition of terminal alkynes and azides [J].
Alonso, Francisco ;
Moglie, Yanina ;
Radivoy, Gabriel ;
Yus, Miguel .
TETRAHEDRON LETTERS, 2009, 50 (20) :2358-2362
[2]   Nanoparticles as recyclable catalysts: The frontier between homogeneous and heterogeneous catalysis [J].
Astruc, D ;
Lu, F ;
Aranzaes, JR .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (48) :7852-7872
[3]   Copper-free click chemistry for dynamic in vivo imaging [J].
Baskin, Jeremy M. ;
Prescher, Jennifer A. ;
Laughlin, Scott T. ;
Agard, Nicholas J. ;
Chang, Pamela V. ;
Miller, Isaac A. ;
Lo, Anderson ;
Codelli, Julian A. ;
Bertozzi, Carolyn R. .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2007, 104 (43) :16793-16797
[4]   When CuAAC 'Click Chemistry' goes heterogeneous [J].
Chassaing, S. ;
Beneteau, V. ;
Pale, P. .
CATALYSIS SCIENCE & TECHNOLOGY, 2016, 6 (04) :923-957
[5]   Cellular uptake and trafficking of polydiacetylene micelles [J].
Gravel, Edmond ;
Theze, Benoit ;
Jacques, Isabelle ;
Anilkumar, Parambath ;
Gombert, Karine ;
Duconge, Frederic ;
Doris, Eric .
NANOSCALE, 2013, 5 (05) :1955-1960
[6]   Drug Delivery and Imaging with Polydiacetylene Micelles [J].
Gravel, Edmond ;
Ogier, Julien ;
Arnauld, Thomas ;
Mackiewicz, Nicolas ;
Duconge, Frederic ;
Doris, Eric .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (02) :400-408
[7]   Copper-catalyzed azide-alkyne cycloaddition (CuAAC) and beyond: new reactivity of copper(I) acetylides [J].
Hein, Jason E. ;
Fokin, Valery V. .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (04) :1302-1315
[8]   1.3-DIPOLARE CYCLOADDITIONEN .32. KINETIK DER ADDITIONEN ORGANISCHER AZIDE AN CC-MEHRFACHBINDUNGEN [J].
HUISGEN, R ;
SZEIMIES, G ;
MOBIUS, L .
CHEMISCHE BERICHTE-RECUEIL, 1967, 100 (08) :2494-&
[9]  
Huisgen R., 1963, Angew. Chem. Int. Ed, V2, P565, DOI [10.1002/anie.196305651, DOI 10.1002/ANIE.196305651]
[10]   Cu-free click cycloaddition reactions in chemical biology [J].
Jewett, John C. ;
Bertozzi, Carolyn R. .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (04) :1272-1279