Reusable polymer-supported catalyst for the [3+2] Huisgen cycloaddition in automation protocols

被引:284
|
作者
Girard, C
Önen, E
Aufort, M
Beauvière, S
Samson, E
Herscovici, J
机构
[1] Ecole Natl Super Chim Paris, F-75005 Paris, France
[2] INSERM, U640, F-75006 Paris, France
[3] CNRS, UMR8151, F-75006 Paris, France
[4] Univ Paris 05, Fac Pharm, Unite Pharmacol Chim & Genet, F-75270 Paris, France
[5] CNRS, Chim Mol Paris Ctr, F-75005 Paris, France
关键词
D O I
10.1021/ol060283l
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A polymer-supported catalyst for Huisgen's [3+2] cycloaddition reaction between azides and alkynes was prepared from copper(I) iodide and Amberlyst A-21. This catalyst was then used in an automated synthesis of 1,4-disubstituted 1,2,3-triazoles giving access to these products in good yields. The catalyst has shown good activity, stability, and recycling capabilities.
引用
收藏
页码:1689 / 1692
页数:4
相关论文
共 50 条
  • [31] Microencapsulated osmium tetraoxide. A new recoverable and reusable polymer-supported osmium catalyst for dihydroxylation of olefins
    Nagayama, S
    Endo, M
    Kobayashi, S
    JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (18): : 6094 - 6095
  • [32] A FAST PROCEDURE FOR THE PREPARATION OF BENZIMIDAZOLE DERIVATIVES USING POLYMER-SUPPORTED WITH TRIFLUOROMETHANESULFONIC ACID AS NOVEL AND REUSABLE CATALYST
    Karami, Changiz
    Ghodrati, Keivan
    Izadi, Mina
    Farrokh, Azita
    Jafari, Sedigheh
    Mahmoudiyani, Maryam
    Haghnazari, Nahid
    JOURNAL OF THE CHILEAN CHEMICAL SOCIETY, 2013, 58 (03): : 1914 - 1917
  • [33] Polymer-supported formamides as reusable organocatalysts for allylation of aldehydes with allyltrichlorosilane
    Ogawa, C
    Sugiura, M
    Kobayashi, S
    CHEMICAL COMMUNICATIONS, 2003, (02) : 192 - 193
  • [34] Polymer-supported PPh3 as a reusable organocatalyst for the Mukaiyama aldol and Mannich reaction
    Matsukawa, Satoru
    Fukazawa, Kazuki
    Kimura, Junya
    RSC ADVANCES, 2014, 4 (53) : 27780 - 27786
  • [35] A reusable polymer-supported copper(I) catalyst for triazole click reaction on water: An experimental and computational study
    Bahsis, Lahoucine
    Ben El Ayouchia, Hicham
    Anane, Hafid
    Pascual-Alvarez, Alejandro
    De Munno, Giovanni
    Julve, Miguel
    Stiriba, Salah-Eddine
    APPLIED ORGANOMETALLIC CHEMISTRY, 2019, 33 (04)
  • [36] Copper-doped silica cuprous sulfate (CDSCS) as a highly efficient and new heterogeneous nano catalyst for [3+2] Huisgen cycloaddition
    Rad, Mohammad Navid Soltani
    Behrouz, Somayeh
    Doroodmand, Mohammad Mahdi
    Movahediyan, Abdollah
    TETRAHEDRON, 2012, 68 (38) : 7812 - 7821
  • [37] Polymer-supported bis (2-hydroxyanyl) acetylacetonato molybdenyl Schiff base catalyst as effective, selective and highly reusable catalyst in epoxidation of alkenes
    Grivani, Gholamhossein
    Akherati, Akram
    INORGANIC CHEMISTRY COMMUNICATIONS, 2013, 28 : 90 - 93
  • [38] Chemoselective tetrahydropyranylation of alcohols and phenols using nanoencapsulated FeCl3 in linear polystyrene as a recoverable and reusable polymer-supported catalyst
    Rahmatpour, Ali
    Alijani, Naser
    SYNTHETIC COMMUNICATIONS, 2022, 52 (11-12) : 1397 - 1411
  • [39] Kinetic Resolution of Nitrogen Heterocycles with a Reusable Polymer-Supported Reagent
    Kreituss, Imants
    Murakami, Yuta
    Binanzer, Michael
    Bode, Jeffrey W.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (42) : 10660 - 10663
  • [40] Using a Polymer-Supported Azide Ion in [2+3] Cycloaddition Reaction of Azide Ion with Nitriles
    Zarchi, Mohammad Ali Karimi
    Nazem, Fatemeh
    JOURNAL OF APPLIED POLYMER SCIENCE, 2012, 123 (04) : 1977 - 1982