In-situ-generated palladium nanoparticles in novel ionic liquid: an efficient catalytic system for Heck-Matsuda coupling

被引:6
|
作者
Gaikwad, D. S. [1 ]
Undale, K. A. [1 ]
Patil, D. B. [1 ]
Pore, D. M. [2 ]
Korade, S. N. [2 ]
Kamble, A. A. [3 ]
机构
[1] Vivekanand Coll, Dept Chem, Kolhapur 416003, Maharashtra, India
[2] Shivaji Univ, Dept Chem, Kolhapur 416004, Maharashtra, India
[3] Bharatratna Indira Gandhi Coll Engn, Dept Chem, Solapur 413255, Maharashtra, India
关键词
Heck-Matsuda; Stereospecific; Nanoparticles; Task-specific IL; ONE-POT-SYNTHESIS; CROSS-COUPLINGS; ARENEDIAZONIUM SALTS; IMIDAZOLIUM; WATER; ARYL; COMPLEX; LIGAND; PERSPECTIVES; TOXICITY;
D O I
10.1007/s11164-017-2888-5
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A green, convenient, ecological and recyclable method comprising dual functionalized, task-specific, ionic liquid (IL)-triggered, in situ-generated Pd nanoparticles (NPs) and their catalytic application for Heck-Matsuda coupling of olefins is described. Both arenediazonium tetrafluoroborate and silica sulphate salts are coupled with olefins under ligand-free and aerobic conditions at ambient temperature furnishing excellent yields of products. The Ionic liquid used acts as a reducing as well as stabilizing agent for in situ-generated Pd NPs. The formed NPs were characterized by transmission electron microscopy (TEM) analysis, having a size below 50 nm, and exhibited high catalytic activity. The catalytic system can be reused for eight times effectively without any significant loss of activity. The method was found to be highly stereo-specific, giving exclusively the 'E' isomer.
引用
下载
收藏
页码:4445 / 4458
页数:14
相关论文
共 50 条
  • [1] In-situ-generated palladium nanoparticles in novel ionic liquid: an efficient catalytic system for Heck–Matsuda coupling
    D. S. Gaikwad
    K. A. Undale
    D. B. Patil
    D. M. Pore
    S. N. Korade
    A. A. Kamble
    Research on Chemical Intermediates, 2017, 43 : 4445 - 4458
  • [2] HECK-MATSUDA REACTION UTILIZING IN-SITU GENERATED PALLADIUM ON ALUMINUM PHOSPHATE
    Stern, Therese
    Heyde , Sandra
    Brunner, Heiko
    BULLETIN OF THE CHEMICAL SOCIETY OF ETHIOPIA, 2022, 36 (02) : 423 - 432
  • [3] In Situ Generated Palladium on Aluminum Phosphate as Catalytic System for the Preparation of β,β-Diarylated Olefins by Matsuda-Heck Reaction
    Lucks, Sandra
    Brunner, Heiko
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2017, 21 (11) : 1835 - 1842
  • [4] Benign Arylations of Dimethyl Itaconate via Heck-Matsuda Reaction Utilizing in-Situ Generated Palladium on Aluminum Oxide
    Mateliene , Lauryna
    Knaup, Jan
    von Horsten, Frank
    Gu, Xiaoting
    Brunner, Heiko
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (01) : 127 - 135
  • [5] Carboxymethylcellulose-supported palladium nanoparticles generated in situ from palladium(II) carboxymethylcellulose as an efficient and reusable catalyst for ligand- and base-free Heck-Matsuda and Suzuki-Miyaura couplings
    Xiao, Jinlong
    Lu, Zhangxiu
    Li, Zhipeng
    Li, Yiqun
    APPLIED ORGANOMETALLIC CHEMISTRY, 2015, 29 (09) : 646 - 652
  • [6] Palladium nanoparticles generated from allylpalladium chloride in situ: A simple and highly efficient catalytic system for Mizoroki-Heck reactions
    Wang, Wei
    Yang, Qin
    Zhou, Rong
    Fu, Hai-Yan
    Li, Rui-Xiang
    Chen, Hua
    Li, Xian-Jun
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2012, 697 (01) : 1 - 5
  • [7] Palladium nanoparticles supported on agarose-catalyzed Heck-Matsuda and Suzuki-Miyaura coupling reactions using aryl diazonium salts
    Gholinejad, Mohammad
    APPLIED ORGANOMETALLIC CHEMISTRY, 2013, 27 (01) : 19 - 22
  • [8] Simple, efficient and recyclable palladium catalytic system for Heck reaction in functionalized ionic liquid network
    Liu, Ye
    Li, Min
    Lu, Yong
    Gao, Guo-Hua
    Yang, Qin
    He, Ming-Yuan
    CATALYSIS COMMUNICATIONS, 2006, 7 (12) : 985 - 989
  • [9] Multi-functionalized ionic liquid with in situ-generated palladium nanoparticles for Suzuki, Heck coupling reaction: a comparison with deep eutectic solvents
    Gaikwad, D. S.
    Undale, K. A.
    Patil, D. B.
    Pore, D. M.
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2019, 16 (02) : 253 - 261
  • [10] Multi-functionalized ionic liquid with in situ-generated palladium nanoparticles for Suzuki, Heck coupling reaction: a comparison with deep eutectic solvents
    D. S. Gaikwad
    K. A. Undale
    D. B. Patil
    D. M. Pore
    Journal of the Iranian Chemical Society, 2019, 16 : 253 - 261