Efficient coupling of heteroaryl halides with arylboronic acids in the presence of a palladium-tetraphosphine catalyst

被引:71
作者
Feuerstein, M [1 ]
Doucet, H [1 ]
Santelli, M [1 ]
机构
[1] Fac Sci & Tech St Jerome, CNRS, Organ Synth Lab, F-13397 Marseille, France
关键词
tetraphosphine; palladium; suzuki-coupling; arylboronic acids; heteroaryl halides;
D O I
10.1016/j.jorganchem.2003.07.005
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Cis,cis,cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane: 1/2[PdCl(C3H5)](2) system catalyses the Suzuki cross-coupling of heteroaryl halides with a range of arylboronic acids with very high ratio substrate/catalyst in good yields. Substrates such as pyridines, quinolines, thiophenes, an indole, pyrimidines or a furane have been used successfully. (C) 2003 Elsevier B.V. All rights reserved.
引用
收藏
页码:327 / 336
页数:10
相关论文
共 39 条
  • [1] Orthopalladated triaryl phosphite complexes as highly active catalysts in biaryl coupling reactions
    Albisson, DA
    Bedford, RB
    Lawrence, SE
    Scully, PN
    [J]. CHEMICAL COMMUNICATIONS, 1998, (19) : 2095 - 2096
  • [2] PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ARYLBORONIC ACIDS WITH PI-DEFICIENT HETEROARYL CHLORIDES
    ALI, NM
    MCKILLOP, A
    MITCHELL, MB
    REBELO, RA
    WALLBANK, PJ
    [J]. TETRAHEDRON, 1992, 48 (37) : 8117 - 8126
  • [3] Palladacyclic phosphinite complexes as extremely high activity catalysts in the Suzuki reaction
    Bedford, RB
    Welch, SL
    [J]. CHEMICAL COMMUNICATIONS, 2001, (01) : 129 - 130
  • [4] PALLADACYCLES AS EFFICIENT CATALYSTS FOR ARYL COUPLING REACTIONS
    BELLER, M
    FISCHER, H
    HERRMANN, WA
    OFELE, K
    BROSSMER, C
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (17): : 1848 - 1849
  • [5] Berthiol F, 2003, EUR J ORG CHEM, V2003, P1091
  • [6] Arylated pyridines:: Suzuki reactions of O-substituted 2,6-dihalogenated-3-hydroxypyridines
    Chapman, GM
    Stanforth, SP
    Tarbit, B
    Watson, MD
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (05): : 581 - 582
  • [7] Synthesis of 6-aryl-2,4-diamino-pyrimidines and triazines using palladium catalysed Suzuki cross-coupling reactions
    Cooke, G
    de Cremiers, HA
    Rotello, VM
    Tarbit, B
    Vanderstraeten, PE
    [J]. TETRAHEDRON, 2001, 57 (14) : 2787 - 2789
  • [8] Efficient Heck vinylation of aryl halides catalyzed by a new air-stable palladium-tetraphosphine complex
    Feuerstein, M
    Doucet, H
    Santelli, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (17) : 5923 - 5925
  • [9] Feuerstein M, 2002, SYNLETT, P1807
  • [10] Tetraphosphine/palladium-catalysed Suzuki cross-coupling with sterically hindered aryl bromides and arylboronic acids
    Feuerstein, M
    Doucet, H
    Santelli, M
    [J]. TETRAHEDRON LETTERS, 2001, 42 (38) : 6667 - 6670