Application of Magnetic Nanoparticles Supported Pd Catalysts in C—C Bond Formation Reactions

doi:10.11944/j.issn.1000-0518.2015.01.140078

Chinese Journal of Applied Chemistry ›› 2015, Vol. 32 ›› Issue (1): 19-26.DOI: 10.11944/j.issn.1000-0518.2015.01.140078

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Application of Magnetic Nanoparticles Supported Pd Catalysts in C—C Bond Formation Reactions

FENG Cuilan^{a, *}, LIU Jianping^{a, b}, GUI Jianzhou^b, LIU Lantao^{a, *}

^aChemistry & Chemical Engineering,Shangqiu Normal University,Shangqiu,He'nan 476000,China;
^bSchool of Chemistry and Material Science,Liaoning Shihua University,Fushun,Liaoning 113000,China

Received:2014-03-14 Revised:2014-05-19 Published:2015-01-06 Online:2015-01-06
Contact: Corresponding author:FENG Cuilan, associate professor; Tel/Fax:0370-2595072; E-mail:fengcuilanfan@163.com; Research interests:green organocatalytic reaction
Supported by:
Supported by the National Natural Science Foundation of China(No.21102087), Key Technologies R & D Program of He'nan Scientific and Technological Committee(No.112102210477), Funding Scheme for Young Teachers in Colleges and Universities in He'nan Province(No.2011GGJS-157)

Abstract

Abstract:

Due to their high catalytic activity and easily recoverable characters, the magnetic nanoparitcles(MNPs) supported catalysts have received extensive attention in academy as well as industry. Thus, they have been developed into a kind of sustainable nanocatalysts with wide application prospect. In this paper, the recent development in the synthesis and application of MNPs supported palladium catalysts for a variety of C—C coupling reactions such as Suzuki coupling reactions, Heck coupling reactions, etc., is reviewed. A brief outlook of their developments is also presented.

Key words: magnetic nanoparticles, supported Pd catalysts, C-C coupling reaction, Suzuki coupling reaction, Heck coupling reaction

CLC Number:

O621.2

FENG Cuilan, LIU Jianping, GUI Jianzhou, LIU Lantao. Application of Magnetic Nanoparticles Supported Pd Catalysts in C—C Bond Formation Reactions[J]. Chinese Journal of Applied Chemistry, 2015, 32(1): 19-26.

References

[1] Nasir B R B,Barma R S. Magnetically Retrievable Catalysts for Organic Synthesis[J]. Chem Commun ,2013,48(20):752-770.
[2] Gawande M B,Branco P S,Varma R S. Nano-magnetite (Fe 3 O 4 ) as a Support for Recyclable Catalysts in the Development of Sustainable Methodologies[J]. Chem Soc Rev ,2013,42(8):3371-3393.
[3] Gawande M B,Rathi A K,Branco P S, et al . Sustainable Utility of Magnetically Recyclable Nano-Catalysts in Water:Applications in Organic Synthesis[J]. Appl Sci ,2013,3:656-674.
[4] Taladriz-Blanco P,Hervé s P,Pérez-Juste J. Supported Pd Nanoparticles for Carbon-Carbon Coupling Reactions[J]. Top Catal ,2013,56:1154-1170.
[5] SHEN Bin,WANG Yongan,WANG Zhifei, et al . Catalytic Activity of an Oxime Carbapalladacycle Complex Grafted onto Superparamagnetically Mesoporous Nanoparticles for the Heck Reaction[J]. Acta Phys-Chim Sin ,2010,26(7):1860-1866(in Chinese).
沈彬,王永安,王志飞,等. 超顺磁性介孔纳米颗粒嫁接肟Pd环络合物对Heck反应的催化活性[J]. 物理化学学报,2010,26(7):1860-1866.
[6] Jin M J,Lee D H. A Practical Heterogeneous Catalyst for the Suzuki, Sonogashira, and Stille Coupling Reactions of Unreactive Aryl Chlorides[J]. Angew Chem Int Ed ,2010,49(6):1119-1122.
[7] Yang J H,Wang D F,Liu W D, et al . Palladium Supported on a Magnetic Microgel:an Efficient and Recyclable Catalyst for Suzuki and Heck Reactions in Water[J]. Green Chem ,2013,15(12):3429-3437.
[8] Beygzadeh M,Alizadeh A,Khodaei M M, et al . Biguanide/Pd(OAc)₂Immobilized on Magnetic Nanoparticle as a Recyclable Catalyst for the Heterogeneous Suzuki Reaction in Aqueous Media[J]. Catal Commun ,2013,32:86-91.
[9] Taher A,Kim J B,Jung J Y. Highly Active and Magnetically Recoverable Pd-NHC Catalyst Immobilized on Fe 3 O 4 Nanoparticle-Ionic Liquid Matrix for Suzuki Reaction in Water[J]. Synlett ,2009,(15):2477-2482.
[10] Jin X D,Zhang K Y,Sun J, et al . Magnetite Nanoparticles Immobilized Salen Pd(Ⅱ) as a Green Catalyst for Suzuki Reaction[J]. Catal Commun ,2012,26:199-203.
[11] Phan N T S,Le H V. Superparamagnetic Nanoparticles-Supported Phosphine-Free Palladium Catalyst for the Sonogashira Coupling Reaction[J]. J Mol Catal A : Chem ,2011,334:130-138.
[12] Bui N T,Dang T B,Le H V, et al . Suzuki Reaction of Aryl Bromides Using a Phosphine-Free Magnetic Nanoparticle-Supported Palladium Catalyst[J]. Chinese J Catal ,2011,32(11/12):1667-1676.
[13] Zhang Q,Su H,Luo J, et al . “Click” Magnetic Nanoparticle-Supported Palladium Catalyst:a Phosphine-Free, Highly Efficient and Magnetically Recoverable Catalyst for Suzuki-Miyaura Coupling Reactions[J]. Catal Sci Technol ,2013,3:235-243.
[14] Choi K H,Shokouhimehr M. Heterogeneous Suzuki Cross-Coupling Reaction Catalyzed by Magnetically Recyclable Nanocatalyst[J]. Bull Korean Chem Soc ,2013,34(5):1477-1480.
[15] Zhang F W,Niu J R,Wang H B, et al . Palladium was Supported on Superparamagnetic Nanoparticles:a Magnetically Recoverable Catalyst for Heck Reaction[J]. Mater Res Bull ,2012,47(2):504-507.
[16] Ma M L,Zhang Q Y,Yin D Z, et al . Preparation of High-Magnetization Fe 3 O 4 -NH₂-Pd(0) Catalyst for Heck Reaction[J]. Catal Commun ,2012,17:168-172.
[17] Vaddula B R,Saha A A,Leazera J, et al . A Simple and Facile Heck-Type Arylation of Alkenes with Diaryliodonium Salts Using Magnetically Recoverable Pd-Catalyst[J]. Green Chem ,2012,14:2133-2136.
[18] Wang P,Zhang F W,Long Y, et al . Stabilizing Pd on the Surface of Hollow Magnetic Mesoporous Spheres:a Highly Active and Recyclable Catalyst for Hydrogenation and Suzuki Coupling Reactions[J]. Catal Sci Technol ,2013,3:1618-1624.
[19] Wang P,Liu H Z,Liu M M, et al . Immobilized Pd Complexes Over HMMS as Catalysts for Heck Cross-Coupling and Selective Hydrogenation Reactions[J]. New J Chem ,2014,38:1138-1143
[20] Niu J R,Liu M M,Wang P, et al . Stabilizing Pd Ⅱ on Hollow Magnetic Mesoporous Spheres: a Highly Active and Recyclable Catalyst for Carbonylative Cross-Coupling and Suzuki Coupling Reactions[J]. New J Chem ,2014,(Accepted).
[21] Wang P,Liu H Z,Niu J R, et al . Entangled Pd Complexes over Fe 3 O 4 @SiO₂as Supported Catalysts for Hydrogenation and Suzuki Reactions[J]. Catal Sci Technol ,2014,(Accepted).
[22] Zhang F W,Jin J,Zhong X, et al . Pd Immobilized on Amine-Functionalized Magnetite Nanoparticles:a Novel and Highly Active Catalyst for Hydrogenation and Heck Reactions[J]. Green Chem ,2011,13:1238-1243.
[23] Li P H,Wang L,Zhang L, et al . Magnetic Nanoparticles-Supported Palladium:a Highly Efficient and Reusable Catalyst for the Suzuki,Sonogashira, and Heck Reactions[J]. Adv Synth Catal ,2012,354(7):1307-1318.
[24] Du Q W,Zhang W,Ma H, et al . Immobilized Palladium on Surface-Modified Fe 3 O 4 /SiO₂Nanoparticles: as a Magnetically Separable and Stable Recyclable High-Performance Catalyst for Suzuki and Heck Cross-Coupling Reactions[J]. Tetrahedron ,2012,68(18):3577-3584.
[25] Rosario-Amorin D,Gaboyard M,Clérac R, et al . Metallodendritic Grafted Core-Shell γ -Fe₂O 3 Nanoparticles Used as Recoverable Catalysts in Suzuki C-C Coupling Reactions[J]. Chem Eur J ,2012,18:3305-3315.
[26] Shokouhimehr M,Lee J E,Han S I, et al . Magnetically Recyclable Hollow Nanocomposite Catalysts for Heterogeneous Reduction of Nitroarenes and Suzuki Reactions[J]. Chem Commun ,2013,49(42):4779-4781.
[27] Sun J,Dong Z P,Sun X, et al . Pd Nanoparticles in Hollow Magnetic Mesoporous Spheres: High Activity, and Magnetic Recyclability[J]. J Mol Catal A : Chem ,2013,367:46-51.
[28] Zhu M Y,Diao G W. Magnetically Recyclable Pd Nanoparticles Immobilized on Magnetic Fe 3 O 4 @C Nanocomposites:Preparation, Characterization, and Their Catalytic Activity toward Suzuki and Heck Coupling Reactions[J]. J Phys Chem C ,2011,115(50):24743-24749.
[29] Li R,Zhang P,Huang Y M, et al . Pd-Fe 3 O 4 @C Hybrid Nanoparticles:Preparation, Characterization, and Their High Catalytic Activity toward Suzuki Coupling Reactions[J]. J Mater Chem ,2012,22:22750-22755.
[30] Senapapati K K,Roy S,Borgohain C, et al . Palladium Nanoparticle Supported on Cobalt Ferrite:an Efficient Magnetically Separable Catalyst for Ligand Free Suzuki Coupling[J]. J Mol Catal A : Chem ,2012,352:128-134.
[31] Zhou S,Johnson M,Veinot J G C. Iron/iron Oxide Nanoparticles:a Versatile Support for Catalytic Metals and Their Application in Suzuki-Miyaura Cross-Coupling Reactions[J]. Chem Commun ,2010,46:2411-2413.
[32] Li W,Zhang B L,Li X J, et al . Preparation and Characterization of Novel Immobilized Fe 3 O 4 @SiO₂@MSiO₂-Pd(0) Catalyst with Large Pore-Size Mesoporous for Suzuki Coupling Reaction[J]. Appl Catal A : General ,2013,459(24):65-72.
[33] Fujii S,Hamasaki H,Abe H, et al . One-Step Synthesis of Magnetic Iron-Conducting Polymer-Palladium Ternary Nanocomposite Microspheres with Applications as a Recyclable Catalyst[J]. J Mater Chem A ,2013,1(14):4427-4430.
[34] Li S Z,Zhang W,So M H, et al . One-Pot Solvothermal Synthesis of Pd/Fe 3 O 4 Nanocomposite and its Magnetically Recyclable and Efficient Catalysis for Suzuki Reactions[J]. J Mol Catal A : Chem ,2012,359:81-87.
[35] Ko S,Jang J. A Highly Efficient Palladium Nanocatalyst Anchored on a Magnetically Functionalized Polymer-Nanotube Support[J]. Angew Chem Int Ed ,2006,45:7564-7567.
[36] Hu J F,Wang Y P,Han M, et al . A Facile Preparation of Palladium Nanoparticles Supported on Magnetite/S-Graphene and Their Catalytic Application in Suzuki-Miyaura Reaction[J]. Catal Sci Technol ,2012,2(11):2332-2340.
[37] FENG Cuilan,XU Haiyun,XU Maotian, et al . Progress in the Application of Magnetic Nanoparticles Supported Catalysts[J]. Chinese J Synth Chem ,2012,20(2):131-136(in Chinese).
冯翠兰,徐海云,徐茂田,等. 磁性纳米颗粒负载催化剂的应用研究进展[J]. 合成化学,2012,20(2):131-136.
[38] FENG Cuilan,XU Haiyun,XU Maotian, et al . Synthesis and Application of Magnetically Recoverable Palladium Catalyst[J]. Chem Reag ,2012,34(10):927-929,940(in Chinese).
冯翠兰,徐海云,徐茂田,等. 易磁分离钯催化剂的合成及应用研究[J]. 化学试剂,2012,34(10):927-929,940.
[39] FENG Cuilan,XU Haiyun,LIU Lantao, et al . Catalytic Synthesis of Diaryl Ethers with Magnetically Recoverable Fe 3 O 4 Nanoparticles Under Solvent-free and Ligand-free Conditions[J]. Chinese J Appl Chem ,2014,31(5):536-540(in Chinese).
冯翠兰,徐海云,刘澜涛,等. 易磁分离磁性纳米Fe 3 O 4 在无溶剂和无配体条件下催化合成二芳醚[J]. 应用化学,2014,31(5):536-540.
[40] FENG Cuilan,XU Haiyun,XU Maotian, et al . Synthesis of Hydroxyl-Modified Magnetic Nanometer Fe 3 O 4 Supported Palladium Catalyst[J]. Guangdong Chem Ind ,2011,38(8):286-287(in Chinese).
冯翠兰,徐海云,徐茂田,等. 羟基修饰的磁性纳米Fe 3 O 4 负载钯催化剂的合成[J]. 广东化工,2011,38(8):286-287.

Application of Magnetic Nanoparticles Supported Pd Catalysts in C—C Bond Formation Reactions

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