Nano-silica supported palladium catalyst: Synthesis, characterization and application of its activity in Sonogashira cross-coupling reactions

被引:24
作者
Dehbanipour, Zahra [1 ]
Moghadam, Majid [1 ]
Tangestaninejad, Shahram [1 ]
Mirkhani, Valiollah [1 ]
Mohammadpoor-Baltork, Iraj [1 ]
机构
[1] Univ Isfahan, Catalysis Div, Dept Chem, Esfahan 8174673441, Iran
关键词
Sonogashira cross-coupling; Palladium complex; Nano silica; Aryl halide; COPPER-FREE SONOGASHIRA; ONE-POT SYNTHESIS; EFFICIENT CATALYST; TERMINAL ALKYNES; HIGHLY EFFICIENT; ARYL HALIDES; BASE COMPLEX; WATER; BENZOTHIAZOLES; CHLORIDES;
D O I
10.1016/j.jorganchem.2017.10.006
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
This study deals about preparation of palladium(II) complex of 3,5-bis(2-benzothiazolyl) pyridine supported on nano silica functionalized with trimethoxysilylpropyl chloride, Pd(II)Cl-2-BTP@TMSP-nSiO(2). The synthesized heterogeneous catalyst was characterized by FT-IR, UV-Vis spectroscopies, field emission scanning electron microscopy, energy dispersive X-ray analysis, transmission electron microscopy and elemental analysis. Furthermore, the Pd(II)Cl-2-BTP@TMSP-nSiO(2) was found as a highly efficient catalyst in the Sonogashira cross-coupling of aryl halides (iodides, bromides and chlorides) with phenyl acetylene. This heterogeneous catalyst was easily recyclable and reused several times without significant loss of reactivity. Finally, its catalytic activity was compared with homogeneous catalyst to demonstrate the effect of supporting on the catalytic activity. (C) 2017 Elsevier B.V. All rights reserved.
引用
收藏
页码:5 / 12
页数:8
相关论文
共 39 条
[1]  
[Anonymous], 2013, PRACT ASP FUTUR DEV, DOI DOI 10.1002/9783527648283.CH3
[2]   A novel 1,2,4-triazine-functionalized polystyrene resin-supported Pd(II) complex: A copper- and solvent-free highly efficient catalyst for Sonogashira coupling reactions [J].
Bakherad, Mohammad ;
Bahramian, Bahram ;
Jajarmi, Saeideh .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2014, 749 :405-409
[3]   Carbazole-corrole and carbazole-prophyrin dyads: synthesis, fluorescence and electrochemical studies [J].
Balsukuri, Naresh ;
Das, Sudipta ;
Gupta, Iti .
NEW JOURNAL OF CHEMISTRY, 2015, 39 (01) :482-491
[4]   Mild Pd/Cu-Catalyzed Sila- Sonogashira Coupling of (Hetero)aryl Bromides with (Hetero)arylethynylsilanes under PTC Conditions [J].
Bellina, Fabio ;
Lessi, Marco .
SYNLETT, 2012, (05) :773-777
[5]   The sonogashira reaction:: A booming methodology in synthetic organic chemistry [J].
Chinchilla, Rafael ;
Najera, Carmen .
CHEMICAL REVIEWS, 2007, 107 (03) :874-922
[6]   Recent advances in Sonogashira reactions [J].
Chinchilla, Rafael ;
Najera, Carmen .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5084-5121
[7]   Microwave-Promoted Copper-Free Sonogashira-Hagihara Couplings of Aryl Imidazolylsulfonates in Water [J].
Civicos, Jose F. ;
Alonso, Diego A. ;
Najera, Carmen .
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (01) :203-208
[8]   Efficient and convenient copper-free Pd(OAc)2/Ruphos-catalyzed Sonogashira coupling in the preparation of corfin analogues [J].
Dasaradhan, Changalaraya ;
Kumar, Yadavalli Suneel ;
Prabakaran, Kamalakannan ;
Khan, Faziur-Rahman Nawaz ;
Jeong, Euh Duck ;
Chung, Eun Hyuk .
TETRAHEDRON LETTERS, 2015, 56 (06) :784-788
[9]  
Dehbani Z., 2017, POLYHEDRON
[10]   Palladium-based catalytic systems for the synthesis of conjugated enynes by Sonogashira reactions and related alkynylations [J].
Doucet, Henri ;
Hierso, Jean-Cyrille .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (06) :834-871