A novel water-soluble m-TPPTC ligand:: Steric and electronic features -: Recent developments in Pd- and Rh-catalyzed C-C bond formations

被引：63
作者：
Genin, E
Amengual, R
Michelet, V
Savignac, M
Jutand, A
Neuville, L
Genêt, JP
机构：
[1] Ecole Natl Super Chim Paris, Lab Synthese Select Organ & Prod Nat, UMR 7573, F-75231 Paris 05, France
[2] Ecole Normale Super, Dept Chim, UMR 8640, F-75231 Paris, France
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2004年 / 346卷 / 13-15期
关键词：
palladium; phosphane basicity; recycling; rhodium; Sonogashira cross-couplings; water-soluble ligand;
D O I：
10.1002/adsc.200404218
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
The steric and electronic features of the novel water-soluble phosphane m-TPPTC have been determined using NMR, IR and UV-VIS spectroscopic methods and compared to the well-known sulfonated analogue TPPTS. The higher basicity of m-TPPTC compared to TPPTS had an influence (selectivity and efficiency) either on Pd- or Rh-catalyzed C-C bond formations reactions. The Sonogashira copper-free cross-couplings of aryl iodides and ortho-functionalized aryl iodides were efficiently performed using the carboxylated phosphane m-TPPTC leading to the alkynes in high yields. The Pd/m-TPPTC system was found to be efficiently recycled under mild biphasic conditions in the Sonogashira reaction.
引用
收藏
页码：1733 / 1741
页数：9
相关论文
共 120 条
  • [1] AN EFFICIENT PALLADIUM-CATALYZED REACTION OF VINYL AND ARYL HALIDES OR TRIFLATES WITH TERMINAL ALKYNES
    ALAMI, M
    FERRI, F
    LINSTRUMELLE, G
    [J]. TETRAHEDRON LETTERS, 1993, 34 (40) : 6403 - 6406
  • [2] THE CHEMISTRY OF HETEROARYLPHOSPHORUS COMPOUNDS .15. P-31 NUCLEAR MAGNETIC-RESONANCE STUDIES OF THE DONOR PROPERTIES OF HETEROARYLPHOSPHINES TOWARDS SELENIUM AND PLATINUM(II)
    ALLEN, DW
    TAYLOR, BF
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1982, (01): : 51 - 54
  • [3] C(sp2)-C(sp) and C(sp)-C(sp) coupling reactions catalyzed by oxime-derived palladacycles
    Alonso, DA
    Nájera, C
    Pacheco, MC
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (9-10) : 1146 - 1158
  • [4] A copper- and amine-free Sonogashira-type coupling procedure catalyzed by oxime palladacycles
    Alonso, DA
    Nájera, C
    Pacheco, MC
    [J]. TETRAHEDRON LETTERS, 2002, 43 (51) : 9365 - 9368
  • [5] EVIDENCE OF THE FORMATION OF ZEROVALENT PALLADIUM FROM PD(OAC)2 AND TRIPHENYLPHOSPHINE
    AMATORE, C
    JUTAND, A
    MBARKI, MA
    [J]. ORGANOMETALLICS, 1992, 11 (09) : 3009 - 3013
  • [6] RATES AND MECHANISM OF THE FORMATION OF ZEROVALENT PALLADIUM COMPLEXES FROM MIXTURES OF PD(OAC)(2) AND TERTIARY PHOSPHINES AND THEIR REACTIVITY IN OXIDATIVE ADDITIONS
    AMATORE, C
    CARRE, E
    JUTAND, A
    MBARKI, MA
    [J]. ORGANOMETALLICS, 1995, 14 (04) : 1818 - 1826
  • [7] Anionic Pd(0) and Pd(II) intermediates in palladium-catalyzed Heck and cross-coupling reactions
    Amatore, C
    Jutand, A
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (05) : 314 - 321
  • [8] NEW SYNTHETIC APPLICATIONS OF WATER-SOLUBLE ACETATE PD/TPPTS CATALYST GENERATED IN-SITU - EVIDENCE FOR A TRUE PD(0) SPECIES INTERMEDIATE
    AMATORE, C
    BLART, E
    GENET, JP
    JUTAND, A
    LEMAIREAUDOIRE, S
    SAVIGNAC, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) : 6829 - 6839
  • [9] Amatore C., 2002, HDB ORGANOPALLADIUM, P943
  • [10] Amengual R, 2002, ADV SYNTH CATAL, V344, P393, DOI 10.1002/1615-4169(200206)344:3/4<393::AID-ADSC393>3.0.CO
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