2-Aminopyridine functionalized cellulose based Pd nanoparticles: An efficient and ecofriendly catalyst for the Suzuki cross-coupling reaction

Abstract

A palladium catalyst supported on 2-aminopyridine functionalized cellulose was synthesized and fully characterized by inductively coupled plasma atomic emission spectroscopy, transmission electron microscope, Fourier transform infrared spectroscopy, thermogravimetric analysis and X-ray photoelectron spectrometry. This catalyst can be applied in the Suzuki cross-coupling reaction of aryl halides with arylboronic acids in 50% ethanol to afford biaryls in good yields, and easily recycled by simple filtration after reaction without the loss of metal Pd.

Graphical abstract

Keywords

cellulose-supported / 2-aminopyridine / palladium nanoparticles / ecofriendly catalyst / Suzuki cross-coupling reaction

References

[1] Yan L F, Zhao Y, Gu Q, Li W. Isolation of highly purity cellulose from wheat straw using a modified aqueous biphasic system. Frontiers of Chemical Science and Engineering, 2012, 6(3): 282–291

[2] David L K. Biopolymers from Renewable Resources. Berlin: Springer, 1998, 1–29

[3] Habibi Y, Lucia A A, Rojas O J. Cellulose nanocrystals: Chemistry, self-Assembly, and applications. Chemical Reviews, 2010, 110(6): 3479–3500

[4] Árpád M, Attila P. The use of polysaccharides and derivatives in palladium-catalyzed coupling reactions. Catalysis Science and Technology, 2014, 4(2): 295–310

[5] Françoise Q, Agnès C. Cellulose: A new bio-support for aqueous phase catalysts. Chemical Communications, 2001, 1(16): 21–22

[6] Navjot J, Ravinderpal K S, Princy G, Satya P. Nano Pd(0) supported on cellulose: A highly efficient and recyclable heterogeneous catalyst for the Suzuki coupling and aerobic oxidation of benzyl alcohols under liquid phase catalysis. International Journal of Biological Macromolecules, 2011, 49(5): 930–935

[7] Ciprian M C, Alexandre F D, Audrey M. Cellulose nanocrystallites as an efficient support for nanoparticles of palladium: Application for catalytic hydrogenation and Heck coupling under mild conditions. Green Chemistry, 2011, 13(2): 288–291

[8] Kumar N S, Sreedhar B, Reddy K R, Kantam M L. N-Arylation of nitrogen heterocycles with aryl halides and arylboronic acids catalyzed by cellulose supported copper(0). Journal of Molecular Catalysis A Chemical, 2006, 252(1): 136–141

[9] Song Z Q, Wang H, Niu Y F, Liu X, Han J Y. Selective conversion of cellulose to hexitols over bi-functional Ru-supported sulfated zirconia and silica-zirconia catalysts. Frontiers of Chemical Science and Engineering, 2015, 9(4): 461–466

[10] Huang Y, Wang T H, Ji M Z, Yang J Z, Zhu C L, Sun D P. Simple preparation of carbonized bacterial cellulose-Pt composite as a high performance electrocatalyst for direct methanol fuel cells (DMFC). Materials Letters, 2014, 128(10): 93–96

[11] Fu J P, Li D W, Li G H, Huang F L, Wei Q F. Carboxymethyl cellulose assisted immobilization of silver nanoparticles onto cellulose nanofibers for the detection of catechol. Journal of Electroanalytical Chemistry, 2015, 738: 92–99

[12] Xia H F, Lin D Q, Yao S J. Spherical cellulose-nickel powder composite matrix customized for expanded bed application. Journal of Applied Polymer Science, 2007, 104(2): 740–747

[13] Mohamed A H, Brahim B, Larbi E F, Ahmad M, Claudio S, Stefano G, Morena N, Mustapha A A. Colloidal nickel(0)-carboxymethyl cellulose particles: A biopolymer-inorganic catalyst for hydrogenation of nitro-aromatics and carbonyl compounds. Catalysis Communications, 2013, 32(5): 92–100

[14] Du Q W, Li Y Q. Air-stable, recyclable, and time-efficient diphenylphosphinite cellulose-supported palladium nanoparticles as a catalyst for Suzuki-Miyaura reactions. Beilstein Journal of Organic Chemistry, 2011, 7(6): 378–385

[15] Wang X X, Xu Y J, Wang F, Wei Y P. Functionalized cellulose-supported triphenylphosphine and its application in Suzuki cross-coupling reactions. Journal of Applied Polymer Science, 2014, 131(6): 41427–41435

[16] Wang X X, Hu P B, Xue F J, Wei Y P. Cellulose-supported N-heterocyclic carbene-palladium catalyst: Synthesis and its applications in the Suzuki cross-coupling reaction. Carbohydrate Polymers, 2014, 114: 476–483

[17] Keshipour S, Shojaei S, Shaabani A. Palladium nano-particles supported on ethylenediamine functionalized cellulose as a novel and efficient catalyst for the Heck and Sonogashira couplings in water. Cellulose (London, England), 2013, 20(2): 973–980

[18] Sun J W, Huang J T, Zhang J Q, Zheng S H. The synthesis of epoxide resin with alkylaminopyridine functions. Journal of Applied Polymer Science, 1995, 55(13): 1865–1866

[19] Zhao P N, Hao J C. 2,6-Diaminopyridine-imprinted polymer and its potency to hair-dye assay using graphene/ionic liquid electrochemical sensor. Biosensors and Bioelectronics, 2015, 64: 277–284

[20] Alam T, Tarannum H, Kumar N, Kamaluddin N. Interaction of 2-amino-, 3-amino-, and 4-aminopyridines with chromium and manganese ferrocyanides. Journal of Colloid and Interface Science, 2000, 224(1): 133–139

[21] Yang Y F, Chen Y Y. Sorption behaviors of five kinds of functional polymers bearing aminopyridine groups for Ir(IV) and Ru(IV) ions. Journal of Functional Polymers, 1996, 1: 1–8

[22] Mondal P, Banerjee S, Roy A S, Islam S M. In situ prepared mesoporous silica nanosphere supported palladium(II) 2-aminopyridine complex catalyst for Suzuki-Miyaura cross-coupling reaction in water. Journal of Materials Chemistry, 2012, 22(38): 20434–20442

[23] Lyakin O Y, Ottenbacher R V, Bryliakov K P, Talsi E P. Asymmetric epoxidations with H₂O₂ on Fe and Mn aminopyridine catalysts: Probing the nature of active species by combined electron paramagnetic resonance and enantioselectivity study. ACS Catalysis, 2012, 2(6): 1196–1202

[24] Mohammad B, Hosein A A, Farzaneh G. ChemInform abstract: Synthesis and characterization of the 2-methylaminopyridine-functionalized polystyrene resin-supported Pd(II) catalyst for the Mizoroki-Heck and Sonogashira reactions in water. Journal‒Chinese Chemical Society Taipei, 2014, 61(2): 279–284

[25] Motokura K, Itagaki S, Iwasawa Y, Akimitsu M, Toshihide B. Silica-supported aminopyridinium halides for catalytic transformations of epoxides to cyclic carbonates under atmospheric pressure of carbon dioxide. ChemInform, 2010, 41(41): 1876–1880

[26] Rahn K, Diamantoglou M, Klemm D, Berghmans H, Heinze T. Homogeneous synthesis of cellulose p-toluenesulfonates in N,N-dimethylacetamide/LiCl solvent system. Angewandte Makromolekulare Chemie, 1996, 238(1): 143–163

[27] Chen Y, Yan Z. Synthesis and characterization of polyacrylonitrile-2-amino-2-thiazoline resin and its sorption behaviors for noble metal ions. Reactive & Functional Polymers, 2003, 55(1): 89–98

[28] Kurt R, Sanjines R, Karimi A, Lévy, F. Structural and mechanical properties of CNx thin films prepared by magnetron sputtering. Diamond & Related Materials, 2000, 9(s3‒6): 566–572

[29] Ji C, Song S, Wang C, Chen H. Preparation and adsorption properties of chelating resins containing 3-aminopyridine and hydrophilic spacer arm for Hg(II). Chemical Engineering Journal, 2010, 165(2): 573–580

[30] Yu Z, Chen Y, Wang C, Wei Y M. Immobilization of 5-aminopyridine-2-tetrazole on cross-linked polystyrene for the preparation of a new adsorbent to remove heavy metal ions from aqueous solution. Journal of Hazardous Materials, 2014, 276(9): 129–137

[31] Gammon W J, Kraft O, Reilly A C, Holloway B C. Experimental comparison of N(1s) X-ray photoelectron spectroscopy binding energies of hard and elastic amorphous carbon nitride films with reference organic compounds. Carbon, 2003, 41(10): 1917–1923

[32] Xiao J L, Lu Z X, Li Y Q. Carboxymethylcellulose-supported palladium nanoparticles generated in situ from palladium(II) carboxymethylcellulose: An efficient and reusable catalyst for Suzuki-Miyaura and Mizoroki-Heck reactions. Industrial & Engineering Chemistry Research, 2015, 54(3): 790–797

RIGHTS & PERMISSIONS

Higher Education Press and Springer-Verlag Berlin Heidelberg