Suzuki cross-coupling reactions between alkenylboronic acids and aryl bromides catalysed by a tetraphosphane-palladium catalyst

被引:74
作者
Peyroux, E [1 ]
Berthiol, F [1 ]
Doucet, H [1 ]
Santelli, M [1 ]
机构
[1] Fac Sci & Tech St Jerome, CNRS, Lab Synth Organ Assoc, F-13397 Marseille, France
关键词
alkenes; aryl halides; catalysis; cross-coupling; palladium; phosphanes;
D O I
10.1002/ejoc.200300627
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A range of alkenylboronic acids undergo Suzuki cross-coupling with aryl bromides in good yields in the presence of [PdCl(C3H5)](2)/cis,cis,cis-1,2,3,4-tetrakis[(diphenylphosphanyl)methyl]cyclopentane as a catalyst. A wide variety of 1-arylprop-1-enes, 2-arylprop-1-enes, 2-arylbut-1-enes and 1,1-diarylethylene or styrene derivatives have been prepared. Moreover, the reaction tolerates several functions, such as acetyl, formyl, nitrile or nitro. Furthermore, this catalyst can be used at low loading, even for reactions of sterically hindered substrates. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
引用
收藏
页码:1075 / 1082
页数:8
相关论文
共 50 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] Highly efficient palladium-catalyzed boronic acid coupling reactions in water: Scope and limitations
    Badone, D
    Baroni, M
    Cardamone, R
    Ielmini, A
    Guzzi, U
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (21) : 7170 - 7173
  • [3] Highly active catalysts for the Suzuki coupling of aryl chlorides
    Bedford, RB
    Cazin, CSJ
    [J]. CHEMICAL COMMUNICATIONS, 2001, (17) : 1540 - 1541
  • [4] Palladacyclic phosphinite complexes as extremely high activity catalysts in the Suzuki reaction
    Bedford, RB
    Welch, SL
    [J]. CHEMICAL COMMUNICATIONS, 2001, (01) : 129 - 130
  • [5] 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
  • [6] Berthiol F, 2003, EUR J ORG CHEM, V2003, P1091
  • [7] Heck reaction of aryl halides with linear or cyclic alkenes catalysed by a tetraphosphine/palladium catalyst
    Berthiol, F
    Doucet, H
    Santelli, M
    [J]. TETRAHEDRON LETTERS, 2003, 44 (06) : 1221 - 1225
  • [8] BRAUN J, 1966, B SOC CHIM FR, P2557
  • [9] Chahen L, 2003, SYNLETT, P1668
  • [10] Palladium-tetraphosphine complex: an efficient catalyst for the coupling of aryl halides with alkynes
    Feuerstein, M
    Berthiol, F
    Doucet, H
    Santelli, M
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (13) : 2235 - 2237