Ultrasonic synthesis of supported palladium nanoparticles for room-temperature Suzuki–Miyaura coupling
Source abstract
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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Research context
OpenAlex topics: Catalytic Cross-Coupling Reactions · Nanomaterials for catalytic reactions · Covalent Organic Framework Applications
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References (45)
Show source-provided 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 20:3437–344010.1016/S0040-4039(01)95429-2 ↗
2. Miyaur N, Suzuki A (1995) Review: palladium-catalyzed cross-coupling reactions of organoboron compouds. Chem Rev 95:2457–248310.1021/cr00039a007 ↗
3. Kozlowski MC, Morgan BJ, Linton EC (2009) Review: total synthesis of chiral biaryl natural products by asymmetric biaryl coupling. Chem Soc Rev 38:3193–320710.1039/b821092f ↗
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 132:11278–1128710.1021/ja104297g ↗
5. Enthaler S (2011) Review: palladium-catalysed hydroxylation and alkoxylation. Chem Soc Rev 40:4912–492410.1039/c1cs15085e ↗
6. Tagata T, Nishid M (2003) Review: palladium charcoal-catalyzed Suzuki–Miyaura coupling to obtain arylpyridines and arylquinolines. J Org Chem 68:9412–941510.1021/jo034970r ↗
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 12:724–72610.1021/ol9028034 ↗
8. Fihr A, Bouhrara M, Nekoueishahrak B, Basseta JM, Polshettiwar V (2011) Review: nanocatalysts for Suzuki cross-coupling reactions. Chem Soc Rev 40:5181–520310.1039/c1cs15079k ↗
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 13:1260–126610.1039/c0gc00176g ↗
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 40:5151–516910.1039/c1cs15088j ↗
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 337:39–4410.1016/j.molcata.2011.01.011 ↗
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
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 37:27–3110.1016/j.catcom.2013.03.006 ↗
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 54:1331–133710.1016/j.tetlet.2012.11.140 ↗
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 1:12909–1291810.1039/c3ta12512b ↗
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 273:156–16610.1016/j.jcat.2010.05.009 ↗
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 128:197–20210.1007/s10562-008-9732-x ↗
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 367:264–27110.1016/j.jcis.2011.10.036 ↗
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 366:170–17710.1016/j.colsurfa.2010.06.009 ↗
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 20:2086–209410.1021/cm071194l ↗
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 11:1781–178610.1039/b916261p ↗
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 363:245–25310.1016/j.molcata.2012.06.016 ↗
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 156:105–11210.1016/j.matchemphys.2015.02.032 ↗
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 14:9343–934910.1039/c2cp40792b ↗
25. Darroudi M, Zak AK, Muhamad MR, Huang NM, Hakimi M (2012) Review: green synthesis of colloidal silver nanoparticles by sonochemical method. Mater Lett 66:117–12010.1016/j.matlet.2011.08.016 ↗
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 23:255606–25561610.1088/0957-4484/23/25/255606 ↗
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 145:1388–139510.1007/s10562-015-1537-0 ↗
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 110:383–38710.1021/jp0535801 ↗
29. Nemamcha A, Moumeni H, Rehspringe JL (2009) Review: PVP protective mechanism of palladium nanoparticles obtained by sonochemical process. Phys Proced 2:713–71710.1016/j.phpro.2009.11.015 ↗
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 36:160910.1088/0022-3727/36/13/328 ↗
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 319:498–50410.1016/j.jcis.2007.11.037 ↗
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 179:708–71510.1016/j.jssc.2005.11.023 ↗
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 52:350–35610.1346/CCMN.2004.0520310 ↗
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 286:184–19210.1016/j.jcat.2011.11.001 ↗
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 22:15953–1595910.1039/c2jm32702c ↗
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 7:18247–1825610.1021/acsami.5b05715 ↗
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 128:8376–837710.1021/ja0612100 ↗
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 165:661–66710.1016/j.apcatb.2014.10.072 ↗
39. Tao Q, He H, Frost RL, Yuan P, Zhu J (2009) Review: nanomaterials based upon silylated layered double hydroxides. Appl Surf Sci 255:4334–434010.1016/j.apsusc.2008.11.030 ↗
40. Hongping H, Ray FL, Jianxi Z (2004) Review: infrared Study of HDTMA+ intercalated montmorillonite. Spectrochim Acta Part A 60:2853–285910.1016/j.saa.2003.09.028 ↗
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 149:166–17210.1016/j.saa.2015.04.012 ↗
42. Okitsu K, Bandow H, Maeda Y, Nagata Y (1996) Review: sonochemical preparation of ultrafine palladium particles. Chem Mater 8:315–31710.1021/cm950285s ↗
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 12:3006–301110.1021/cm0001915 ↗
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 12:325–32910.1016/j.ultsonch.2004.06.007 ↗
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 163:135–14210.1016/j.apcatb.2014.07.053 ↗