Evidence that SCS pincer Pd(II) complexes are only precatalysts in Heck catalysis and the implications for catalyst recovery and reuse

被引:281
作者
Yu, KQ
Sommer, W
Richardson, JM
Weck, M [1 ]
Jones, CW
机构
[1] Georgia Inst Technol, Sch Chem & Biomol Engn, Atlanta, GA 30332 USA
[2] Georgia Inst Technol, Sch Chem & Biochem, Atlanta, GA 30332 USA
关键词
biphasic catalysis; Heck reaction; immobilization; leaching; palladium; pincer complex;
D O I
10.1002/adsc.200404264
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
SCS-pincer Pd(II) complexes have been covalently immobilized onto porous silica, cross-linked polymer (Merrifield resin) and soluble poly(norbornene) supports via either amide or urea linkages and evaluated in the Heck coupling of iodobenzene with n-butyl acrylate. Kinetic experiments and poisoning studies indicate that in all cases the pincer complexes merely act as precatalysts. Contrary to literature reports, there is no evidence for catalysis by the intact amide-linked SCS-Pd(II) complexes under any conditions studied here.
引用
收藏
页码:161 / 171
页数:11
相关论文
共 81 条
  • [1] A perspective on nanocluster catalysis: Polyoxoanion and (n-C4H9N+ stabilized Ir(O) (similar to 300) nanocluster 'soluble heterogeneous catalysts'
    Aiken, JD
    Lin, Y
    Finke, RG
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1996, 114 (1-3) : 29 - 51
  • [2] Albrecht M, 2001, ANGEW CHEM INT EDIT, V40, P3750, DOI 10.1002/1521-3773(20011015)40:20<3750::AID-ANIE3750>3.0.CO
  • [3] 2-6
  • [4] HETEROGENEOUS CATALYSIS IN ORGANIC-CHEMISTRY .10. EFFECT OF THE CATALYST SUPPORT ON THE REGIOCHEMISTRY OF THE HECK ARYLATION REACTION
    AUGUSTINE, RL
    OLEARY, ST
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1995, 95 (03) : 277 - 285
  • [5] Silica-supported imine palladacycles - recyclable catalysts for the Suzuki reaction?
    Bedford, RB
    Cazin, CSJ
    Hursthouse, MB
    Light, ME
    Pike, KJ
    Wimperis, S
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 633 (1-2) : 173 - 181
  • [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] Beller M, 1999, EUR J INORG CHEM, P1121
  • [8] Palladium(II) containing hydrotalcite as an efficient heterogeneous catalyst for Heck reaction
    Bennur, TH
    Ramani, A
    Bal, R
    Chanda, BM
    Sivasanker, S
    [J]. CATALYSIS COMMUNICATIONS, 2002, 3 (10) : 493 - 496
  • [9] Palladium-catalyzed C-C coupling under thermomorphic conditions
    Bergbreiter, DE
    Osburn, PL
    Wilson, A
    Sink, EM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (38) : 9058 - 9064
  • [10] Tridentate SCS palladium(II) complexes: New, highly stable, recyclable catalysts for the heck reaction
    Bergbreiter, DE
    Osburn, PL
    Liu, YS
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (41) : 9531 - 9538