Iron(0), rhodium(I) and palladium(II) complexes with p-(N,N-dimethylaminophenyl) diphenylphosphine and the application of the palladium complex as a catalyst for the Suzuki-Miyaura cross-coupling reaction

被引:15
|
作者
Sarmah, Chandan [1 ]
Borah, Malabika [1 ]
Das, Pankaj [1 ]
机构
[1] Dibrugarh Univ, Dept Chem, Dibrugarh 786004, Assam, India
关键词
aminophosphine ligand; metal complex; Suzuki-Miyaura reaction; aqueous solvent; room temperature; N-HETEROCYCLIC CARBENES; HIGHLY-ACTIVE CATALYST; ARYL CHLORIDES; COORDINATION CHEMISTRY; HEMILABILE LIGANDS; EFFICIENT; DERIVATIVES; HYDROFORMYLATION; AMINATION; BEHAVIOR;
D O I
10.1002/aoc.1801
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The reaction of p-(N,N-dimethylaminophenyl)diphenylphosphine [PPh2(p-C6H4NMe2)] with [Fe-3(CO)(12)], [Rh(CO)(2)Cl](2) and PdCl2 resulted in three new mononuclear complexes, {Fe(CO)(4)(n(1)-(P)-PPh2(p-C6H4NMe2)]} (1a), trans-{Rh(CO)Cl[n(1)-(P)-PPh2(p-C6H4NMe2)](2)} (2) and trans-{PdCl2[n(1)-(P)-PPh2(p-C6H4NMe2)](2)} (3), respectively. A small amount of dinuclear nonmetal-metal bonded complex, {Fe-2(CO)8[mu,-(P,N)-PPh2(p-C6H4NMe2)]} (1b), was also isolated as a side product in the reaction of (Fe-3(CO)(12)]. The complexes were characterized by elemental analyses, mass, IR, UV-vis, H-1, C-13 (except 1b) and P-31{H-1} NMR spectroscopy. The Pd complex 3 effectively catalyzes the Suzuki - Miyaura cross-coupling reactions of aryl halides with arylboronic acids in water - isopropanol (1 : 1) at room temperature. Excellent yields (up to 99% isolated yield) were achieved. The effects of different solvents, bases, catalyst quantities were also evaluated. Copyright (C) 2011 John Wiley & Sons, Ltd.
引用
收藏
页码:552 / 558
页数:7
相关论文
共 50 条
  • [41] Water-Soluble Palladium(II) Sulfonated Thiosemicarbazone Complexes: Facile Synthesis and Preliminary Catalytic Studies in the Suzuki-Miyaura Cross-Coupling Reaction in Water
    Matsinha, Leah C.
    Mao, Jincheng
    Mapolie, Selwyn F.
    Smith, Gregory S.
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2015, (24) : 4088 - 4094
  • [42] Practical synthesis of 6-aryluridines via palladium(II) acetate catalyzed Suzuki-Miyaura cross-coupling reaction
    Shih, Yu-Chiao
    Chien, Tun-Cheng
    TETRAHEDRON, 2011, 67 (21) : 3915 - 3923
  • [43] In situ Generation of Efficient Palladium N-heterocyclic Carbene Catalysts Using Benzimidazolium Salts for the Suzuki-Miyaura Cross-coupling Reaction
    Akkoc, Senem
    Gok, Yetkin
    Ilhan, Ilhan Ozer
    Kayser, Veysel
    CURRENT ORGANIC SYNTHESIS, 2016, 13 (05) : 761 - 766
  • [44] Palladium(II)-N-heterocyclic carbene complex derived from proline towards Suzuki-Miyaura coupling reaction in water at room temperature
    Tang, Yi-Qiang
    Lv, Huan
    Lu, Jian-Mei
    Shao, Li-Xiong
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2011, 696 (13) : 2576 - 2579
  • [45] (N-Heterocyclic carbene) ion-pair palladium complexes: Suzuki-Miyaura cross-coupling studies in neat water under mild conditions
    Chen, Ming-Tsz
    Lin, Yu-Hsuan
    Jian, Kun-Han
    APPLIED ORGANOMETALLIC CHEMISTRY, 2020, 34 (12)
  • [46] Silica-acac-supported palladium nanoparticles as an efficient and reusable heterogeneous catalyst in the Suzuki-Miyaura cross-coupling reaction in water
    Hajepour, Abdol Reza
    Shirdashtzade, Zohre
    Azizi, Ghobad
    JOURNAL OF CHEMICAL SCIENCES, 2014, 126 (01) : 85 - 93
  • [47] Silica-acac-supported palladium nanoparticles as an efficient and reusable heterogeneous catalyst in the Suzuki-Miyaura cross-coupling reaction in water
    Hajipour A.R.
    Shirdashtzade Z.
    Azizi G.
    Hajipour, A.R. (haji@cc.iut.ac.ir), 1600, Springer (126): : 85 - 93
  • [48] Carboxyethylsilanetriol-Functionalized Al-MIL-53-Supported Palladium Catalyst for Enhancing Suzuki-Miyaura Cross-Coupling Reaction
    Liang, Yucang
    Ning, Xin
    Zhen, Yanzhong
    MOLECULES, 2025, 30 (03):
  • [49] Palladium Nanoparticles Immobilized on Poly(vinyl chloride)-Supported Pyridinium as an Efficient and Recyclable Catalyst for Suzuki-Miyaura Cross-Coupling Reaction
    Zhou, Bo
    Li, Yi-Qun
    E-JOURNAL OF CHEMISTRY, 2011, 8 (04) : 1490 - 1497
  • [50] Hollow-Shell-Structured Mesoporous Silica-Supported Palladium Catalyst for an Efficient Suzuki-Miyaura Cross-Coupling Reaction
    Mohammed, Abdulelah Taher Ali
    Wang, Lijian
    Jin, Ronghua
    Liu, Guohua
    Tan, Chunxia
    CATALYSTS, 2021, 11 (05)