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

被引:285
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 19 条
  • [1] A microwave-assisted click chemistry synthesis of 1,4-disubstituted 1,2,3-triazoles via a copper(I)-catalyzed three-component reaction
    Appukkuttan, P
    Dehaen, W
    Fokin, VV
    Van der Eycken, E
    [J]. ORGANIC LETTERS, 2004, 6 (23) : 4223 - 4225
  • [2] Hit and lead generation:: Beyond high-throughput screening
    Bleicher, KH
    Böhm, HJ
    Müller, K
    Alanine, AI
    [J]. NATURE REVIEWS DRUG DISCOVERY, 2003, 2 (05) : 369 - 378
  • [3] Polymer-supported copper complex for C-N and C-O cross-coupling reactions with aryl boronic acids
    Chiang, GCH
    Olsson, T
    [J]. ORGANIC LETTERS, 2004, 6 (18) : 3079 - 3082
  • [4] One-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from in situ generated azides
    Feldman, AK
    Colasson, B
    Fokin, VV
    [J]. ORGANIC LETTERS, 2004, 6 (22) : 3897 - 3899
  • [5] Gonthier E, 2003, SYNLETT, P1049
  • [6] Huisgen R., 1984, 1 3 DIPOLAR CYCLOADD
  • [7] Palladium on carbon encapsulated in POEPOP1500:: A resin-supported catalyst for hydrogenation reactions
    Jansson, AM
    Grotli, M
    Halkes, KM
    Meldal, M
    [J]. ORGANIC LETTERS, 2002, 4 (01) : 27 - 30
  • [8] Polymer-supported N-heterocyclic carbene-palladium complex for heterogeneous Suzuki cross-coupling reaction
    Kim, JH
    Kim, JW
    Shokouhimehr, M
    Lee, YS
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (17) : 6714 - 6720
  • [9] The growing impact of click chemistry on drug discovery
    Kolb, HC
    Sharpless, KB
    [J]. DRUG DISCOVERY TODAY, 2003, 8 (24) : 1128 - 1137
  • [10] Kolb HC, 2001, ANGEW CHEM INT EDIT, V40, P2004, DOI 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.3.CO