η2-dba complexes of Pd(0):: The substituent effect in Suzuki-Miyaura coupling

被引:153
作者
Fairlamb, IJS [1 ]
Kapdi, AR [1 ]
Lee, AF [1 ]
机构
[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England
关键词
D O I
10.1021/ol048413i
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The influence of aryl substituents in dibenzylidene acetone (dba) ligands, for Pd(0) complexes, has been evaluated for Suzuki-Miyaura cross-coupling reactions. Electron-withdrawing substituents such as NO2 or CF3 deactivate the catalyst species whereas strongly donating substituents such as Me increase catalytic activity over that of unsubstituted dba ligands.
引用
收藏
页码:4435 / 4438
页数:4
相关论文
共 33 条
  • [1] Unexpected bell-shaped effect of the ligand on the rate of the oxidative addition to palladium(0) complexes generated in situ from mixtures of Pd(dba)2 and para-substituted triarylphosphines
    Amatore, C
    Jutand, A
    Meyer, G
    [J]. INORGANICA CHIMICA ACTA, 1998, 273 (1-2) : 76 - 84
  • [2] RATES AND MECHANISMS OF OXIDATIVE ADDITION TO ZEROVALENT PALLADIUM COMPLEXES GENERATED IN-SITU FROM MIXTURES OF PD0(DBA)2 AND TRIPHENYLPHOSPHINE
    AMATORE, C
    JUTAND, A
    KHALIL, F
    MBARKI, MA
    MOTTIER, L
    [J]. ORGANOMETALLICS, 1993, 12 (08) : 3168 - 3178
  • [3] Identification of the effective palladium(0) catalytic species generated in situ from mixtures of Pd(dba)(2) and bidentate phosphine ligands. Determination of their rates and mechanism in oxidative addition
    Amatore, C
    Broeker, G
    Jutand, A
    Khalil, F
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (22) : 5176 - 5185
  • [4] Role of dba in the reactivity of palladium(0) complexes generated in situ from mixtures of Pd(dba)2 and phosphines
    Amatore, C
    Jutand, A
    [J]. COORDINATION CHEMISTRY REVIEWS, 1998, 178 : 511 - 528
  • [5] Molecularly defined palladium(0) monophosphine complexes as catalysts for efficient cross-coupling of aryl chlorides and phenylboronic acid
    Andreu, MG
    Zapf, A
    Beller, M
    [J]. CHEMICAL COMMUNICATIONS, 2000, (24) : 2475 - 2476
  • [6] Suzuki-Miyaura cross-coupling of aryl and alkyl halides using palladium/imidazolium salt protocols
    Arentsen, K
    Caddick, S
    Geoffrey, F
    Cloke, N
    Herring, AP
    Hitchcock, PB
    [J]. TETRAHEDRON LETTERS, 2004, 45 (17) : 3511 - 3515
  • [7] High-activity catalysts for Suzuki coupling and amination reactions with deactivated aryl chloride substrates: Importance of the palladium source
    Bedford, RB
    Cazin, CSJ
    Coles, SJ
    Gelbrich, T
    Horton, PN
    Hursthouse, MB
    Light, ME
    [J]. ORGANOMETALLICS, 2003, 22 (05) : 987 - 999
  • [8] Homeopathic ligand-free palladium as a catalyst in the Heck reaction. A comparison with a palladacycle
    de Vries, AHM
    Mulders, JMCA
    Mommers, JHM
    Henderickx, HJW
    de Vries, JG
    [J]. ORGANIC LETTERS, 2003, 5 (18) : 3285 - 3288
  • [9] 2-Pyrones possessing antimicrobial and cytotoxic activities
    Fairlamb, IJS
    Marrison, LR
    Dickinson, JM
    Lu, FJ
    Schmidt, JP
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (15) : 4285 - 4299
  • [10] Palladium-catalysed alkynylations of 2-pyrone (pyran-2-one) halides
    Fairlamb, IJS
    Lu, FJ
    Schmidt, JP
    [J]. SYNTHESIS-STUTTGART, 2003, (16): : 2564 - 2570