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Ultrasonic synthesis of supported palladium nanoparticles for room-temperature Suzuki–Miyaura coupling

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Abstract

Palladium nanoparticles (Pd NPs) supported on the surface of sodium dodecyl sulfonate (SDS)-intercalated layered double hydroxide (LDH) nanocomposites were synthesized by a one-step, facile ultrasonic method. The Pd/SDS–LDH nanocomposites were characterized by UV–visible spectroscopy, X-ray diffraction, transmission electron microscopy, scanning electron microscopy, X-ray photoelectron spectroscopy, N2-adsorption, Fourier transform infrared spectroscopy, and inductively coupled plasma optical emission spectrometry. The Pd NPs had an average size of 3.56 nm and were uniformly dispersed on the SDS–LDHs surface. The conversion of 4-bromotoluene catalyzed by Pd0.02/SDS–LDHs reached 98.16 % with 0.1 mmol % catalyst at room temperature without any phase transfer agents, toxic solvents, or inert atmosphere; this conversion was much higher than that of Pd0.02/SDS–LDHs prepared without ultrasound. This was attributed to the high dispersion and size uniformity. Notably, Pd0.05/SDS–LDHs had a much higher catalytic activity than that of commercial Pd/C catalyst with the same Pd content due to the strong interaction between the Pd species and the SDS–LDHs in the Pd/SDS–LDH nanocomposites. These catalysts could be easily separated by centrifugation, and could be recycled five times with little activity loss.

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References

  1. Miyaura N, Yamada K, Suzuki A (1979) Review: a new stereospecific cross-coupling by the palladium-catalyzed reaction of 1-alkenylboranes with 1-alkenyl or 1-alkynyl halides. Tetrahedron Lett 20:3437–3440

    Article  Google Scholar 

  2. Miyaur N, Suzuki A (1995) Review: palladium-catalyzed cross-coupling reactions of organoboron compouds. Chem Rev 95:2457–2483

    Article  Google Scholar 

  3. Kozlowski MC, Morgan BJ, Linton EC (2009) Review: total synthesis of chiral biaryl natural products by asymmetric biaryl coupling. Chem Soc Rev 38:3193–3207

    Article  Google Scholar 

  4. Shen X, Jones GO, Watson DA, Bhayana B, Buchwald SL (2010) Review: enantioselective synthesis of axially chiral biaryls by the Pd-catalyzed Suzuki–Miyaura reaction: substrate scope and quantum mechanical investigations. J Am Chem Soc 132:11278–11287

    Article  Google Scholar 

  5. Enthaler S (2011) Review: palladium-catalysed hydroxylation and alkoxylation. Chem Soc Rev 40:4912–4924

    Article  Google Scholar 

  6. Tagata T, Nishid M (2003) Review: palladium charcoal-catalyzed Suzuki–Miyaura coupling to obtain arylpyridines and arylquinolines. J Org Chem 68:9412–9415

    Article  Google Scholar 

  7. Ackermann L, Barfüsser S, Pospech J (2010) Review: palladium-catalyzed direct arylations, alkenylations, and benzylations through C–H bond cleavages with sulfamates or phosphates as electrophiles. Org Lett 12:724–726

    Article  Google Scholar 

  8. Fihr A, Bouhrara M, Nekoueishahrak B, Basseta JM, Polshettiwar V (2011) Review: nanocatalysts for Suzuki cross-coupling reactions. Chem Soc Rev 40:5181–5203

    Article  Google Scholar 

  9. Liu C, Ni Q, Bao F, Qiu JS (2011) Review: a simple and efficient protocol for a palladium-catalyzed ligand-free Suzuki reaction at room temperature in aqueous DMF. Green Chem 13:1260–1266

    Article  Google Scholar 

  10. Fortman GC, Nolan SP (2011) Review: N-heterocyclic carbene (NHC) ligands and palladium in homogeneous cross-coupling catalysis: a perfect union. Chem Soc Rev 40:5151–5169

    Article  Google Scholar 

  11. Metin Ö, Durap F, Aydemir M, Özkar S (2011) Review: palladium (0) nanoclusters stabilized by poly (4-styrenesulfonic acid-co-maleic scid) as an effective catalyst for Suzuki–Miyaura cross-coupling reactions in water. J Mol Catal A: Chem 337:39–44

    Article  Google Scholar 

  12. Pagliar M, Pandarus V, Ciriminna R, Beland F, Demma Carà P (2012) Review: heterogeneous versus homogeneous palladium catalysts for cross-coupling reactions. Chem Cat Chem 4:432–445

    Google Scholar 

  13. Feng GF, Liu FJ, Lin C, Li W, Wang S, Qi C (2013) Review: crystalline mesoporous γ-Al2O3 supported palladium: novel and efficient catalyst for Suzuki–Miyaura reaction under controlled microwave heating. Catal Commun 37:27–31

    Article  Google Scholar 

  14. Kumbhar A, Jadhav S, Kamble S, Rashinkar G, Salunkhe R (2013) Review: palladium supported hybrid cellulose-aluminum oxide composite for Suzuki–Miyaura cross coupling reaction. Tetrahedron Lett 54:1331–1337

    Article  Google Scholar 

  15. Siamaki AR, Lin Y, Woodberry K, Connellc JW, Frank Gupton B (2013) Review: palladium nanoparticles supported on carbon nanotubes from solventless preparations: versatile catalysts for ligand-free Suzuki cross coupling reactions. J Mater Chem A 1:12909–12918

    Article  Google Scholar 

  16. Okumura K, Tomiyama T, Okuda S, Yoshida H, Niwa M (2010) Review: origin of the excellent catalytic activity of Pd loaded on ultra-stable Y zeolites in Suzuki–Miyaura reactions. J Catal 273:156–166

    Article  Google Scholar 

  17. Harish S, Mathiyarasu J, Phani KLN, Yegnaraman V (2009) Review: synthesis of conducting polymer supported Pd nanoparticles in aqueous medium and catalytic activity towards 4-nitrophenol reduction. Catal Lett 128:197–202

    Article  Google Scholar 

  18. Zhang P, Qian G, Xu ZP, Shi H, Ruan X, Yang J, Frost RLP (2012) Review: effective adsorption of sodium dodecylsulfate (SDS) by hydrocalumite (CaAl-LDH-Cl) induced by self-dissolution and re-precipitation mechanism. J Colloid Interface Sci 367:264–271

    Article  Google Scholar 

  19. Chuang YH, Liu CH, Tzou YM, Chang JS, Chiang PN, Wang MK (2010) Review: comparison and characterization of chemical surfactants and bio-surfactants intercalated with layered double hydroxides (LDHs) for removing naphthalene from contaminated aqueous solutions. Colloids Surf A 366:170–177

    Article  Google Scholar 

  20. Gérardin C, Kostadinova D, Coq B, Tichit D (2008) Review: LDH nanocomposites with different guest entities as precursors of supported Ni catalysts. Chem Mater 20:2086–2094

    Article  Google Scholar 

  21. Amali AJ, Rana RK (2009) Review: stabilisation of Pd (0) on Surface functionalised Fe3O4 nanoparticles: magnetically recoverable and stable recyclable catalyst for hydrogenation and Suzuki–Miyaura reactions. Green Chem 11:1781–1786

    Article  Google Scholar 

  22. Uberman PM, Pérez LA, Lacconi GI, Martín SE (2012) Review: PVP-stabilized palladium nanoparticles electrochemically obtained as effective catalysts in aqueous medium Suzuki–Miyaura reaction. J Mol Catal A Chem 363:245–253

    Article  Google Scholar 

  23. Upadhyay RK, Soin N, Saha S, Barman A, Roy SS (2015) Review: fast and facile preparation of CTAB based gels and their applications in Au and Ag nanoparticles synthesis. Mater Chem Phys 156:105–112

    Article  Google Scholar 

  24. Fenger R, Fertitta E, Kirmse H, Thünemann AF, Rademann K (2012) Review: size dependent catalysis with CTAB-stabilized gold nanoparticles. Phys Chem Chem Phys 14:9343–9349

    Article  Google Scholar 

  25. Darroudi M, Zak AK, Muhamad MR, Huang NM, Hakimi M (2012) Review: green synthesis of colloidal silver nanoparticles by sonochemical method. Mater Lett 66:117–120

    Article  Google Scholar 

  26. Tang S, Vongehr S, Zheng Z, Ren H, Meng X (2012) Review: facile and rapid synthesis of spherical porous palladium nanostructures with high catalytic activity for formic acid electro-oxidation. Nanotechnol 23:255606–255616

    Article  Google Scholar 

  27. Su X, Vinu A, Aldeyab SS, Zhong L (2015) Review: highly uniform Pd nanoparticles supported on g-C3N4 for efficiently catalytic Suzuki–Miyaura reactions. Catal Lett 145:1388–1395

    Article  Google Scholar 

  28. Nemamcha A, Rehspringer JL, Khatmi D (2006) Review: synthesis of palladium nanoparticles by sonochemical reduction of palladium (II) nitrate in aqueous solution. J Phys Chem B 110:383–387

    Article  Google Scholar 

  29. Nemamcha A, Moumeni H, Rehspringe JL (2009) Review: PVP protective mechanism of palladium nanoparticles obtained by sonochemical process. Phys Proced 2:713–717

    Article  Google Scholar 

  30. Kan C, Cai W, Li C, Zhang L, Hofmeister H (2003) Review: ultrasonic synthesis and optical properties of Au/Pd bimetallic nanoparticles in ethylene hlycol. J Phys D Appl Phys 36:1609

    Article  Google Scholar 

  31. Zhu J, Yuan P, He H, Frost R, Tao Q, Shen W, Bostrom T (2008) Review: in situ synthesis of surfactant/silane-modified hydrotalcites. J Colloid Interface Sci 319:498–504

    Article  Google Scholar 

  32. Tao Q, Zhang Y, Zhang X, Yuan P, He H (2006) Review: synthesis and characterization of layered double hydroxides with a high aspect ratio. J Solid State Chem 179:708–715

    Article  Google Scholar 

  33. He H, Frost RL, Deng F, Zhu J, Wen X, Yuan P (2004) Review: conformation of surfactant molecules in the interlayer of montmorillonite studied by 13C MAS NMR. Clays Clay Miner 52:350–356

    Article  Google Scholar 

  34. Harraz FA, El-Hout SE, Killa HM, Ibrahim IA (2012) Review: palladium nanoparticles stabilized by polyethylene glycol: efficient, Recyclable catalyst for hydrogenation of styrene and nitrobenzene. J Catal 286:184–192

    Article  Google Scholar 

  35. Song HM, Moosa BA, Khashab NM (2012) Review: water-dispersable hybrid Au–Pd nanoparticles as catalysts in ethanol oxidation, aqueous phase Suzuki–Miyaura and heck reactions. J Mater Chem 22:15953–15959

    Article  Google Scholar 

  36. Hu B, Cai F, Chen T, Fan M, Song C, Yan X, Shi W (2015) Review: hydrothermal synthesis g-C3N4/nano-InVO4 nanocomposites and enhanced photocatalytic activity for hydrogen production under visible light irradiation. Appl Mater Int 7:18247–18256

    Article  Google Scholar 

  37. Gursky Jennifer A, Blough Sandra D, Luna Cesar, Gomez Clarissa, Luevano Amber N, Gardner Elizabeth A (2006) Review: particle-particle interactions between layered double hydroxide nanoparticles. J Am Chem 128:8376–8377

    Article  Google Scholar 

  38. Sun J, Fu Y, He G, Sun X, Wang X (2015) Review: green Suzuki–Miyaura coupling reaction catalyzed by palladium nanoparticles supported on graphitic carbon nitride. Appl Catal B 165:661–667

    Article  Google Scholar 

  39. Tao Q, He H, Frost RL, Yuan P, Zhu J (2009) Review: nanomaterials based upon silylated layered double hydroxides. Appl Surf Sci 255:4334–4340

    Article  Google Scholar 

  40. Hongping H, Ray FL, Jianxi Z (2004) Review: infrared Study of HDTMA+ intercalated montmorillonite. Spectrochim Acta Part A 60:2853–2859

    Article  Google Scholar 

  41. Zhang P, Wang T, Qian G, Wu D, Frost RL (2015) Review: effective intercalation of sodium dodecylsulfate (SDS) into hydrocalumite: mechanism siscussion via near-infrared and mid-infrared investigations. Spectrochim Acta Part A 149:166–172

    Article  Google Scholar 

  42. Okitsu K, Bandow H, Maeda Y, Nagata Y (1996) Review: sonochemical preparation of ultrafine palladium particles. Chem Mater 8:315–317

    Article  Google Scholar 

  43. Okitsu K, Yue A, Tanabe S, Matsumoto HK (2000) Review: sonochemical preparation and catalytic behavior of highly dispersed palladium nanoparticles on alumina. Chem Mater 12:3006–3011

    Article  Google Scholar 

  44. Rae J, Ashokkumar M, Eulaerts O, von Sonntag C, Reisse J, Grieser F (2005) Review: estimation of ultrasound induced cavitation bubble temperatures in aqueous solutions. Ultrason Sonochem 12:325–329

    Article  Google Scholar 

  45. Lin Q, Li L, Liang S, Liu M, Bi J, Wu L (2015) Review: efficient synthesis of monolayer carbon nitride 2D nanosheet with tunable concentration and enhanced visible-light photocatalytic activities. Appl Catal B 163:135–142

    Article  Google Scholar 

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (Grant No. 21276067), Natural Science Foundation of China- Russian Foundation for Basic Research (NSFC-RFBR, Grant No. 214111301884), Program of International S&T cooperation (Grant No. 2013DFR40570), and Science Foundation of Heilongjiang Academy of Sciences.

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Authors and Affiliations

  1. College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin, 150001, China

    Jiazhe Li & Xuefeng Bai

  2. Institute of Petrochemistry, Heilongjiang Academy of Sciences, Harbin, 150040, China

    Xuefeng Bai

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  1. Jiazhe Li
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Correspondence to Xuefeng Bai.

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Li, J., Bai, X. Ultrasonic synthesis of supported palladium nanoparticles for room-temperature Suzuki–Miyaura coupling. J Mater Sci 51, 9108–9122 (2016). https://doi.org/10.1007/s10853-016-0164-5

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