Novel palladium nanoparticles supported on β-cyclodextrin@graphene oxide as magnetically recyclable catalyst for Suzuki-Miyaura cross-coupling reaction with two different approaches in bio-based solvents

被引:33
作者
Heidari, Bahareh [1 ]
Heravi, Majid M. [1 ]
Nabid, Mohammad Reza [2 ]
Sedghi, Roya [2 ]
Hooshmand, Seyyed Emad [3 ]
机构
[1] Alzahra Univ, Dept Chem, Tehran, Iran
[2] Shahid Beheshti Univ, GC, Dept Polymer & Mat Chem, Fac Chem & Petr Sci, Tehran 1983969411, Iran
[3] Shahid Beheshti Univ, GC, Dept Organ Chem & Oil, Fac Chem & Petr Sci, Tehran 1983969411, Iran
基金
美国国家科学基金会;
关键词
bio-based solvents; host-guest interaction; magnetic graphene oxide (M-GO); palladium nanoparticles; Suzuki-Miyaura cross-coupling reaction; METAL-ORGANIC FRAMEWORK; DEEP EUTECTIC SOLVENTS; HIGHLY EFFICIENT; GREEN SYNTHESIS; PD NANOPARTICLES; C-C; POLYSTYRENE RESIN; REUSABLE CATALYST; CARBENE COMPLEX; CARBON;
D O I
10.1002/aoc.4632
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A novel nanocatalyst was designed and prepared. Initially, the surface of magnetic graphene oxide (M-GO) was modified using thionyl chloride, tris(hydroxymethyl)aminomethane and acryloyl chloride as linkers which provide reactive CC bonds for the polymerization of vinylic monomers. Separately, beta-cyclodextrin (beta-CD) was treated with acryloyl chloride to provide a modified beta-CD. Then, in the presence methylenebisacrylamide as a cross-linker, monomers of modified beta-CD and acrylamide were polymerized on the surface of the pre-prepared M-GO. Finally, palladium acetate and sodium borohydride were added to this composite to afford supported palladium nanoparticles. This fabricated nanocomposite was fully characterized using various techniques. The efficiency of this easily separable and reusable heterogeneous catalyst was successfully examined in Suzuki-Miyaura cross-coupling reactions of aryl halides and boronic acid as well as in modified Suzuki-Miyaura cross-coupling reactions of N-acylsuccinimides and boronic acid in green media. The results showed that the nanocatalyst was efficient in coupling reactions for direct formation of the corresponding biphenyl as well as benzophenone derivatives in green media based on bio-based solvents. In addition, the nanocatalyst was easily separable, using an external magnet, and could be reused several times without significant loss of activity under the optimum reaction conditions.
引用
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页数:13
相关论文
共 97 条
[21]   Nanocatalysts for Suzuki cross-coupling reactions [J].
Fihri, Aziz ;
Bouhrara, Mohamed ;
Nekoueishahraki, Bijan ;
Basset, Jean-Marie ;
Polshettiwar, Vivek .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5181-5203
[22]  
Forgas A, 2016, J AEROSP TECHNOL MAN, V8, P357
[23]   Benign by design: catalyst-free in-water, on-water green chemical methodologies in organic synthesis [J].
Gawande, Manoj B. ;
Bonifacio, Vasco D. B. ;
Luque, Rafael ;
Branco, Paula S. ;
Varma, Rajender S. .
CHEMICAL SOCIETY REVIEWS, 2013, 42 (12) :5522-5551
[24]   Synthesis, X-Ray Crystallography, and Reactions of N-Acyl and N-Carbamoyl Succinimides [J].
Goodman, Cassie A. ;
Eagles, Joel B. ;
Rudahindwa, Leandre ;
Hamaker, Christopher G. ;
Hitchcock, Shawn R. .
SYNTHETIC COMMUNICATIONS, 2013, 43 (16) :2155-2164
[25]   Bio-based solvents: an emerging generation of fluids for the design of eco-efficient processes in catalysis and organic chemistry [J].
Gu, Yanlong ;
Jerome, Francois .
CHEMICAL SOCIETY REVIEWS, 2013, 42 (24) :9550-9570
[26]   Benzimidazole-based palladium-N-heterocyclic carbene: a useful catalyst for C-C cross-coupling reaction at ambient condition [J].
Gupta, Sumanta ;
Basu, Basudeb ;
Das, Sajal .
TETRAHEDRON, 2013, 69 (01) :122-128
[27]  
Heck R. F., 1982, ORG REACT
[28]   Magnetically separable and recyclable Fe3O4@SiO2/isoniazide/Pd nanocatalyst for highly efficient synthesis of biaryls by Suzuki coupling reactions [J].
Heidari, Fatemeh ;
Hekmati, Malak ;
Veisi, Hojat .
JOURNAL OF COLLOID AND INTERFACE SCIENCE, 2017, 501 :175-184
[29]  
Heravi M. M., 2018, ORG LETT
[30]   PdCl2 on modified poly(styrene-co-maleic anhydride): A highly active and recyclable catalyst for the Suzuki-Miyaura and Sonogashira reactions [J].
Heravi, Majid M. ;
Hashemi, Elaheh ;
Beheshtiha, Yahya Shirazi ;
Ahmadi, Shervin ;
Hosseinnejad, Tayebeh .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2014, 394 :74-82