Sonogashira cross-coupling reactions with heteroaryl halides in the presence of a tetraphosphine-palladium catalyst

被引：49
|
作者：
Feuerstein, M
Doucet, H
Santelli, M
机构：
[1] CNRS, Organ Synth Lab, UMR 6180, F-13397 Marseille 20, France
[2] Univ Aix Marseille 3, F-13397 Marseille 20, France
[3] Fac Sci & Tech St Jerome, F-13397 Marseille 20, France
来源：
TETRAHEDRON LETTERS | 2005年 / 46卷 / 10期
关键词：
palladium; catalysis; heteroaryl halide; alkyne; Sonogashira reaction; tetraphosphine;
D O I：
10.1016/j.tetlet.2005.01.044
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Heteroaryl halides undergoes cross-couplings with alkynes in good yields in the presence of [PdCl(C3H5)](2)/cis,cis,cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane as catalyst. A variety of heteroaryl halides such as pyridines, quinolines, a pyrimidine, an indole, a thiophene, or a thiazole have been used successfully. The reaction also tolerates several alkynes such as phenylacetylene and a range of alk-l-ynols. Furthermore, this catalyst can be used at low loading with some substrates. (C) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1717 / 1720
页数：4
相关论文
共 50 条
  • [41] Bio-based palladium catalyst in cryogel for cross-coupling reactions
    Tomarchio, Elisabetta Grazia
    Zagni, Chiara
    Paratore, Vincenzo
    Condorelli, Guglielmo Guido
    Carroccio, Sabrina Carola
    Rescifina, Antonio
    MATERIALS CHEMISTRY FRONTIERS, 2024, 8 (21) : 3558 - 3568
  • [42] Palladium nanoparticles, stabilized by lignin, as catalyst for cross-coupling reactions in water
    Coccia, Francesca
    Tonucci, Lucia
    d'Alessandro, Nicola
    D'Ambrosio, Primiano
    Bressan, Mario
    INORGANICA CHIMICA ACTA, 2013, 399 : 12 - 18
  • [43] Palladium catalyst systems for cross-coupling reactions of aryl chlorides and olefins
    Zapf, A
    Beller, M
    CHEMISTRY-A EUROPEAN JOURNAL, 2001, 7 (13) : 2908 - 2915
  • [44] Stereoselective synthesis of (E,E)-1-arylselenobutadienes by cross-coupling reactions in the presence of palladium catalyst
    Zhu, LS
    Huang, ZZ
    Huang, X
    TETRAHEDRON, 1996, 52 (29) : 9819 - 9822
  • [45] Heck reactions of aryl halides with alk-1-en-3-ol derivatives catalysed by a tetraphosphine-palladium complex
    Berthiol, Florian
    Doucet, Henri
    Santelli, Maurice
    APPLIED ORGANOMETALLIC CHEMISTRY, 2006, 20 (12) : 855 - 868
  • [46] Palladium nanoclusters in Sonogashira cross-coupling: A true catalytic species?
    Thathagar, MB
    Kooyman, PJ
    Boerleider, R
    Jansen, E
    Elsevier, CJ
    Rothenberg, G
    ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (15) : 1965 - 1968
  • [47] Conjugated polymer stabilized palladium nanoparticles as a versatile catalyst for Suzuki cross-coupling reactions for both aryl and heteroaryl bromide systems
    Islam, Rafique Ul
    Witcomb, Michael J.
    Scurrell, Michael S.
    van der Lingen, Elma
    Van Otterlo, Willem
    Mallick, Kaushik
    CATALYSIS SCIENCE & TECHNOLOGY, 2011, 1 (02) : 308 - 315
  • [48] Palladium Nanoparticles Immobilized on Chemically Modified Silica Gel: Efficient Heterogeneous Catalyst for Suzuki, Stille and Sonogashira Cross-Coupling Reactions
    Dutta, Piyali
    Sarkar, Amitabha
    ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (14-15) : 2814 - 2822
  • [49] Highly active and recyclable silica gel-supported palladium catalyst for mild cross-coupling reactions of unactivated heteroaryl chlorides
    Lee, Dong-Hwan
    Jung, Ji-Young
    Jin, Myung-Jong
    GREEN CHEMISTRY, 2010, 12 (11) : 2024 - 2029
  • [50] Palladium Nanoparticles on Assorted Nanostructured Supports: Applications for Suzuki, Heck, and Sonogashira Cross-Coupling Reactions
    Hong, Kootak
    Sajjadi, Mohaddeseh
    Suh, Jun Min
    Zhang, Kaiqiang
    Nasrollahzadeh, Mahmoud
    Jang, Ho Won
    Varma, Rajender S.
    Shokouhimehr, Mohammadreza
    ACS APPLIED NANO MATERIALS, 2020, 3 (03) : 2070 - 2103
12345