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
  • [1] REUSABLE POLYMER-SUPPORTED TERPYRIDINE COPPER COMPLEX FOR [3+2] HUISGEN CYCLOADDITION IN WATER
    Suzuka, Toshimasa
    Ooshiro, Kazumasa
    Kina, Ken'yu
    HETEROCYCLES, 2010, 81 (03) : 601 - 610
  • [2] REUSABLE POLYMER-SUPPORTED 2,2′-BIARYLPYRIDINE-COPPER COMPLEXES FOR HUISGEN [3+2] CYCLOADDITION IN WATER
    Suzuka, Toshimasa
    Kawahara, Yamato
    Ooshiro, Kazumasa
    Nagamine, Takuya
    Ogihara, Kazuhito
    Higa, Matsutake
    HETEROCYCLES, 2012, 85 (03) : 615 - 626
  • [3] COPPER/HP20: NOVEL AND POLYMER-SUPPORTED COPPER CATALYST FOR HUISGEN CYCLOADDITION
    Kitamura, Yoshiaki
    Taniguchi, Kazumi
    Maegawa, Tomohiro
    Monguchi, Yasunari
    Kitade, Yukio
    Sajiki, Hironao
    HETEROCYCLES, 2009, 77 (01) : 521 - 532
  • [4] Functionalized Chitosan as a Green, Recyclable, Biopolymer-Supported Catalyst for the [3+2] Huisgen Cycloaddition
    Chtchigrovsky, Melanie
    Primo, Ana
    Gonzalez, Philippe
    Molvinger, Karine
    Robitzer, Mike
    Quignard, Francoise
    Taran, Frederic
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (32) : 5916 - 5920
  • [5] Cu-Mn bimetallic catalyst for Huisgen [3+2]-cycloaddition
    Yousuf, Syed Khalid
    Mukherjee, Debaraj
    Singh, Baldev
    Maity, Sudip
    Taneja, Subhash Chandra
    GREEN CHEMISTRY, 2010, 12 (09) : 1568 - 1572
  • [6] 2-Oxopiperazine scaffolds by [3+2] cycloaddition reactions with a polymer-supported cyclic nitrone
    Wierschem, F
    Rück-Braun, K
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (11) : 2321 - 2324
  • [7] Ionic polymer supported copper(I): A reusable catalyst for Huisgen's 1,3-dipolar cycloaddition
    Sirion, Uthaiwan
    Bae, Yu Jin
    Lee, Byoung Se
    Chi, Dae Yoon
    SYNLETT, 2008, (15) : 2326 - 2330
  • [8] CuII-Hydrotalcite as an Efficient Heterogeneous Catalyst for Huisgen [3+2] Cycloaddition
    Namitharan, Kayambu
    Kumarraja, Mayilvasagam
    Pitchumani, Kasi
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (12) : 2755 - 2758
  • [9] Reusable and efficient polymer-supported task-specific ionic liquid catalyst for cycloaddition of epoxide with CO2
    Sun, Jian
    Cheng, Weiguo
    Fan, Wei
    Wang, Yaohong
    Meng, Zhenying
    Zhang, Suojiang
    CATALYSIS TODAY, 2009, 148 (3-4) : 361 - 367
  • [10] Carbon-Supported Copper Nanomaterials: Recyclable Catalysts for Huisgen [3+2] Cycloaddition Reactions
    Nia, Ali Shaygan
    Rana, Sravendra
    Doehler, Diana
    Jirsa, Franz
    Meister, Annette
    Guadagno, Liberata
    Koslowski, Eik
    Bron, Michael
    Binder, Wolfgang H.
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (30) : 10763 - 10770