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, Volume 11, Issue 1, pp 287–292 | Cite as

Palladium Supported on Commercial Fumed Silica as Sustainable Catalyst for Suzuki-Miyaura Coupling Reactions

  • Zhen-Wei Kang
  • Zhan-Chen Gao
  • Su-Fang Lv
  • Fei-Bao ZhangEmail author
  • Jian-Xiong JiangEmail author
Original Paper
  • 24 Downloads

Abstract

Palladium nanocatalysts supported on commercial fumed silica were synthesized via a convenient liquid method without any external reductant or surfactants. The catalysts were characterized by inductively coupled plasma-mass spectrometry, X-ray powder diffraction and the transmission electron microscope analysis. Then it was applied for Suzuki-Miyaura cross-coupling reactions. It was found that a number of aryl halides were efficiently catalyzed using these catalysts in aqueous-ethanol under relatively mild condition within 0.5h. Further study showed that the catalyst could be recycled up to 10 times without loss of activity.

Graphical Abstract

Palladium nanocatalysts supported on commercial fumed silica were synthesized and applied for Suzuki-Miyaura cross-coupling reactions. A number of aryl halides were efficiently catalyzed using these catalysts in aqueous-ethanol under relatively mild condition within 0.5h. Further study showed that the catalyst could be recycled up to 10 times without loss of activity.

Keywords

Fumed silica Suzuki reactions Catalyst Silane coupling agent 

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Notes

Acknowledgments

This research was supported by Zhejiang Provincial Natural Science Foundation of China under Grant No. LY18B040003

Supplementary material

12633_2018_9853_MOESM1_ESM.docx (126 kb)
(DOCX 126 KB)

References

  1. 1.
    Sun B, Zhou G, Zhang H (2016) Synthesis, functionalization, and applications of morphology-controllable silica-based nanostructures: A review. Prog Solid State Chem 44(1):1–19CrossRefGoogle Scholar
  2. 2.
    Ciriminna R, Fidalgo A, Pandarus V, Beland F, Ilharco L, Pagliaro M (2013) The sol-gel route to advanced silica-based materials and recent applications. Chem Rev 113(8):6592–6620CrossRefGoogle Scholar
  3. 3.
    Ciriminna R, Sciortino M, Alonzo G, de Schrijver A, Pagliaro M (2011) From molecules to systems: sol-gel microencapsulation in silica-based materials. Chem Rev 111(2):765–789CrossRefGoogle Scholar
  4. 4.
    Begum T, Mondal M, Borpuzari M, Kar R, Kalita G, Gogoi P, Bora U (2017) An immobilized symmetrical bis-(NHC) palladium complex as a highly efficient and recyclable Suzuki-Miyaura catalyst in aerobic aqueous media. Dalton Trans 46(2):539–546CrossRefGoogle Scholar
  5. 5.
    Ge J, Jiang J, Yuan C, Zhang C, Liu M (2017) Palladium nanoparticles stabilized by phosphine ligand for aqueous phase room temperature suzuki-Miyaura coupling. Tetrahedron Lett 58(12):1142–1145CrossRefGoogle Scholar
  6. 6.
    Fukaya N, Ueda M, Onozawa S, Bando K, Miyaji T, Takagi Y, Sakakura T, Yasuda H (2011) Palladium complex catalysts immobilized on silica via a tripodal linker unit with amino groups: preparation, characterization, and application to the Suzuki-Miyaura coupling. J Mol Catal A-Chem 342–343:58–66CrossRefGoogle Scholar
  7. 7.
    Zhang F -B, Lv S -F, Jiang J -X, Ni Y (2014) Preparation of siloxene nanosheet-supported palladium as sustainable catalyst for Mizoroki-Heck reaction. Appl Organomet Chem 28(11):826–830CrossRefGoogle Scholar
  8. 8.
    Jin Y, Li A, Hazelton SG, Liang S, John CL, Selid PD, Pierce DT, Zhao JX (2009) Amorphous silica nanohybrids: Synthesis, properties and applications. Coord Chem Rev 253(23–24):2998–3014CrossRefGoogle Scholar
  9. 9.
    Yokoi T, Kubota Y, Tatsumi T (2012) Amino-functionalized mesoporous silica as base catalyst and adsorbent. Appl Catal A Gen 421–422:14–37CrossRefGoogle Scholar
  10. 10.
    Zheng Z, Song YH, Zheng Q (2017) Interfacial structure and rheology of fumed silica filled polar oligomer nanocomposites. Acta Polym Sin (3):429–453Google Scholar
  11. 11.
    Zhan GW, Zeng HC (2016) Integrated nanocatalysts with mesoporous silica/silicate and microporous MOF materials. Coord Chem Rev 320:181–192CrossRefGoogle Scholar
  12. 12.
    Dong ZP, Yu GQ, Le XD (2015) Gold nanoparticle modified magnetic fibrous silica microspheres as a highly efficient and recyclable catalyst for the reduction of 4-nitrophenol. New J Chem 39(11):8623–8629CrossRefGoogle Scholar
  13. 13.
    Mnasri N, Charnay C, de Menorval LC, Elaloui E, Zajac J (2016) Rod-shaped silica particles derivatized with elongated silver nanoparticles immobilized within mesopores. J Solid State Chem 243:207–214CrossRefGoogle Scholar
  14. 14.
    Mondal P, Banerjee S, Roy AS, Mandal TK, Islam SM (2012) In situ prepared mesoporous silica nanosphere supported palladium(II) 2-aminopyridine complex catalyst for Suzuki-Miyaura cross-coupling reaction in water. J Mater Chem 22(38):20434–20442CrossRefGoogle Scholar
  15. 15.
    Gokulakrishnan N, Karbowiak T, Bellat JP, Vonna L, Saada MA, Paillaud JL, Soulard M, Patarin J, Parmentier J (2013) Improved hydrophobicity of inorganic-organic hybrid mesoporous silica with cage-like pores. Colloid Surf A 421:34–43CrossRefGoogle Scholar
  16. 16.
    Ma TT, Yang RQ, Zheng Z, Song YH (2017) Rheology of fumed silica/polydimethylsiloxane suspensions. J Rheol 61(2):205–215CrossRefGoogle Scholar
  17. 17.
    Kulakowski MP, Pereira FM, Dal Molin DCC (2009) Carbonation-induced reinforcement corrosion in silica fume concrete. Constr Build Mater 23(3):1189–1195CrossRefGoogle Scholar
  18. 18.
    Karimi B, Mansouri F, Mirzaei HM (2015) Recent applications of magnetically recoverable nanocatalysts in C-C and C-X coupling reactions. Chemcatchem 7(12):1736–1789CrossRefGoogle Scholar
  19. 19.
    Yan YB, Chen YT, Jia XL, Yang YH (2014) Palladium nanoparticles supported on organosilane-functionalized carbon nanotube for solvent-free aerobic oxidation of benzyl alcohol. Appl Catal B-Environ 156:385–397CrossRefGoogle Scholar
  20. 20.
    Modak A, Mondal J, Aswal VK, Bhaumik A (2010) A new periodic mesoporous organosilica containing diimine-phloroglucinol, Pd(II)-grafting and its excellent catalytic activity and trans-selectivity in C-C coupling reactions. J Mater Chem 20(37):8099–8106CrossRefGoogle Scholar
  21. 21.
    Song XM, Bai XF, Wu W, Kikhtyanin OV, Zhao AJ, Xiao LF, Su XF, Zhang JW, Wei XM (2017) The effect of palladium loading on the catalytic performance of Pd/SAPO-11 for n-decane hydroisomerization. Mol Catal 433:84–90CrossRefGoogle Scholar
  22. 22.
    Deshmukh K, Ahamed MB, Sadasivuni KK, Ponnamma D, AlMaadeed MAA, Deshmukh RR, Pasha SKK, Polu AR, Chidambaram K (2017) Fumed SiO2 nanoparticle reinforced biopolymer blend nanocomposites with high dielectric constant and low dielectric loss for flexible organic electronics. J Appl Polym Sci 134(5):44427(1–11)CrossRefGoogle Scholar
  23. 23.
    Fihri A, Bouhrara M, Nekoueishahraki B, Basset JM, Polshettiwar V (2011) Nanocatalysts for Suzuki cross-coupling reactions. Chem Soc Rev 40(10):5181–5203CrossRefGoogle Scholar
  24. 24.
    Bej A, Ghosh K, Sarkar A, Knight DW (2016) Palladium nanoparticles in the catalysis of coupling reactions. Rsc Adv 6(14):11446–11453CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media B.V., part of Springer Nature 2018

Authors and Affiliations

  1. 1.Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of EducationHangzhou Normal UniversityHangzhouChina

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