Palladacyclic complexes bearing CNN-type ligands as catalysts in the Heck reaction

被引:26
作者
Chen, CT [1 ]
Chan, YS [1 ]
Tzeng, YR [1 ]
Chen, MT [1 ]
机构
[1] Natl Chung Hsing Univ, Dept Chem, Taichung 402, Taiwan
关键词
D O I
10.1039/b404798b
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Preparations of novel unsymmetrical, tridentate nitrogen ligand precursors, PhN=C(CMe2)(NPh)C=N(CH2)(2)NMe2 (1) and PhN=C(CMe2)(NPh)C=N(CH2)Py(2), are described. Treatment of 1 with 1 molar equiv. (COD)PdCl2 in the presence of NEt3 or with 1 molar equiv. Pd(OAc)(2) affords orthometallated palladium(II) complexes, [PhN=C(CMe2)-(N-eta(1)-Ph)C=N(CH2)(2)NMe2] PdX (X=Cl (3); X=OAc (4)), respectively. Compound 3 can be yielded via the reaction of 4 with an excess of LiCl in methanol. Treatment of 2 with 1 molar equiv. of (COD)PdCl2, Pd(OAc)(2) or Pd(TFA)(2) affords orthometallated palladium(II) complexes, [PhN=C(CMe2)(N-eta(1)-Ph)C=NCH2Py]PdX (X=Cl (5); X=OAc (6); X=TFA (7)), respectively. The crystal and molecular structures are reported for compounds 2, 3, 5 and 6. The application of these novel palladacyclic complexes to the Heck reaction with aryl halide substrates was examined.
引用
收藏
页码:2691 / 2696
页数:6
相关论文
共 39 条
  • [1] Albrecht M, 2001, ANGEW CHEM INT EDIT, V40, P3750, DOI 10.1002/1521-3773(20011015)40:20<3750::AID-ANIE3750>3.0.CO
  • [2] 2-6
  • [3] Phosphine and arsine adducts of N-donor palladacycles as catalysts in the Suzuki coupling of aryl bromides
    Bedford, RB
    Cazin, CSJ
    Coles, SJ
    Gelbrich, T
    Hursthouse, MB
    Scordia, VJM
    [J]. DALTON TRANSACTIONS, 2003, (17) : 3350 - 3356
  • [4] Palladacyclic catalysts in C-C and C-heteroatom bond-forming reactions
    Bedford, RB
    [J]. CHEMICAL COMMUNICATIONS, 2003, (15) : 1787 - 1796
  • [5] 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
  • [6] NC-palladacycles as highly effective cheap precursors for the phosphine-free Heck reactions
    Beletskaya, IP
    Kashin, AN
    Karlstedt, NB
    Mitin, AV
    Cheprakov, AV
    Kazankov, GM
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 622 (1-2) : 89 - 96
  • [7] The heck reaction as a sharpening stone of palladium catalysis
    Beletskaya, IP
    Cheprakov, AV
    [J]. CHEMICAL REVIEWS, 2000, 100 (08) : 3009 - 3066
  • [8] Synthesis, characterization and catalytic activity in Heck-type reactions of orthometallated PdII and PtII complexes derived from (1R,2R)-1,2-diaminocyclohexane
    Bravo, J
    Cativiela, C
    Navarro, R
    Urriolabeitia, EP
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 650 (1-2) : 157 - 172
  • [9] {N-alkyl-N-[pyridin-2-ylmethylene] amine}dichloro palladium(II) complexes:: synthesis, crystal structures and evaluation of their catalytic activities for ethylene polymerization
    Chen, R
    Bacsa, J
    Mapolie, SF
    [J]. POLYHEDRON, 2003, 22 (20) : 2855 - 2861
  • [10] Synthesis of bulky, electron rich hemilabile phosphines and their application in the Suzuki coupling reaction of aryl chlorides
    Clarke, ML
    Cole-Hamilton, DJ
    Woollins, JD
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 2001, (19): : 2721 - 2723