An effective Pd nanocatalyst in aqueous media: stilbene synthesis by Mizoroki-Heck coupling reaction under microwave irradiation

被引:10
|
作者
Garcia, Carolina S. [1 ]
Uberman, Paula M. [1 ]
Martin, Sandra E. [1 ]
机构
[1] Univ Nacl Cordoba, CONICET, INFIQC, Dept Quim Organ,Fac Ciencias Quim, Ciudad Univ, Cordoba, Argentina
来源
关键词
aqueous reaction medium; MAOS; Mizoroki-Heck reaction; Pd nanoparticle; sustainable organic synthesis; PALLADIUM NANOPARTICLES; RESVERATROL DERIVATIVES; CATALYTIC-ACTIVITY; REUSABLE CATALYST; ORGANIC-SYNTHESIS; HIGHLY EFFICIENT; ASYMMETRIC HECK; LIGAND; CARBON; SUZUKI;
D O I
10.3762/bjoc.13.166
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aqueous Mizoroki-Heck coupling reactions under microwave irradiation (MW) were carried out with a colloidal Pd nanocatalyst stabilized with poly(N-vinylpyrrolidone) (PVP). Many stilbenes and novel heterostilbenes were achieved in good to excellent yields starting from aryl bromides and different olefins. The reaction was carried out in a short reaction time and with low catalyst loading, leading to high turnover frequency (TOFs of the order of 100 h(-1)). The advantages like operational simplicity, high robustness, efficiency and turnover frequency, the utilization of aqueous media and simple product work-up make this protocol a great option for stilbene syntheses by Mizoroki-Heck reaction.
引用
收藏
页码:1717 / 1727
页数:11
相关论文
共 50 条
  • [21] Synthesis of surface-active N-heterocyclic carbene ligand and its Pd-catalyzed aqueous Mizoroki-Heck reaction
    Taira, Toshiaki
    Yanagimoto, Takaya
    Sakai, Kenichi
    Sakai, Hideki
    Endo, Akira
    Imura, Tomohiro
    TETRAHEDRON, 2016, 72 (27-28) : 4117 - 4122
  • [22] Synthesis and Characterization of C,C-Type Palladacycles and Their Catalytic Application in Mizoroki-Heck Coupling Reaction
    Lo, Chi Hou
    Lee, Hon Man
    ORGANOMETALLICS, 2018, 37 (07) : 1150 - 1159
  • [23] Bimetallic Ni–Pd Synergism—Mixed Metal Catalysis of the Mizoroki-Heck Reaction and the Suzuki–Miyaura Coupling of Aryl Bromides
    Abhijit A. Kashid
    Dharmaraj J. Patil
    Ramling D. Mali
    Vijay P. Patil
    T. V. Neethu
    Heena K. Meroliya
    Shobha A. Waghmode
    Suresh Iyer
    Catalysis Letters, 2021, 151 : 353 - 358
  • [24] [60]Fullerene-Based Pd(0) Complexes of Phosphorus Ylides as Efficient Nanocatalyst for Homo- and Heterogeneous Mizoroki-Heck Coupling Reactions
    Sabounchei, Seyyed Javad
    Hashemi, Ali
    Hosseinzadeh, Marjan
    Salehzadeh, Sadegh
    Maleki, Farahnaz
    CATALYSIS LETTERS, 2017, 147 (09) : 2319 - 2331
  • [25] Mizoroki-Heck cross-couplings of 2-acetyl-5-bromobenzofuran and aryl halides under microwave irradiation
    Shaaban, Mohamed R.
    Darweesh, Ahmed F.
    Dawood, Kamal M.
    Farag, Ahmad M.
    ARKIVOC, 2010, : 208 - 225
  • [26] Chiral diaminocarbene palladium(II) complexes: Synthesis, reduction to Pd(0) and activity in the Mizoroki-Heck reaction as recyclable catalysts
    Pytkowicz, J
    Roland, S
    Mangeney, P
    Meyer, G
    Jutand, A
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2003, 678 (1-2) : 166 - 179
  • [27] A highly efficient palladium complex supported on MCM-41 nanocatalyst for Mizoroki-Heck and Suzuki-Miyaura cross-coupling reaction
    Nikoorazm, Mohsen
    Khanmoradi, Maryam
    Abdi, Zahra
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2020, 17 (10) : 2577 - 2585
  • [28] Toward safer methodologies for the synthesis of polyheterocyclic systems:: intramolecular arylation of arenes under Mizoroki-Heck reaction conditions
    Hernández, S
    SanMartin, R
    Tellitu, I
    Domínguez, E
    ORGANIC LETTERS, 2003, 5 (07) : 1095 - 1098
  • [30] Synthesis of a novel ZnO nanoplates supported hydrazone-based palladacycle as an effective and recyclable heterogeneous catalyst for the Mizoroki-Heck cross-coupling reaction
    Nouri, Fatemeh
    Rostamizadeh, Shahnaz
    Azad, Mohammad
    INORGANICA CHIMICA ACTA, 2018, 471 : 664 - 673