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Efficient Suzuki coupling over novel magnetic nanoparticle: Fe3O4/L-(+)-tartaric acid/Pd(0)

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Abstract

A new eco-friendly catalytic system is devised for C–C bond formation through Suzuki coupling, using an impressive nanocatalyst (Fe3O4/L-(+)-tartaric acid/Pd-NPs). It contains immobilized palladium (0) onto magnetite nanoparticles, stabilized by tartaric acid, and is characterized by FT-IR, XRD, EDS, SEM, TEM, TGA, and VSM. The catalyst is used in an efficient synthesis of biaryls in EtOH/H2O (1:1), in the presence of K2CO3. Our Fe3O4/tartaric acid/Pd-NPs exhibit magnetic recoverability and reusability for five cycles without measurable loss of its activity.

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References

  1. Kumar S (2019) Recent advances in the schiff bases and N-heterocyclic carbenes as ligands in the cross-coupling reactions: a comprehensive review. J Heterocycl Chem 56:1168–1230. https://doi.org/10.1002/jhet.3504

    Article  CAS  Google Scholar 

  2. Li P, Wang L, Zhang L, Wang G (2012) Magnetic nanoparticles-supported palladium: a highly efficient and reusable catalyst for the Suzuki, Sonogashira, and Heck reactions. Adv Synth Catal 354:1307–1318. https://doi.org/10.1002/adsc.201100725

    Article  CAS  Google Scholar 

  3. Nuri A, Mansoori Y, Bezaatpour A (2019) N-heterocyclic carbene–palladium (II) complex supported on magnetic mesoporous silica for Heck cross-coupling reaction. Appl Organomet Chem 33:e4904. https://doi.org/10.1002/aoc.4904

    Article  CAS  Google Scholar 

  4. Hajipour AR, Kalantari Tarrari M, Jajarmi S (2018) Synthesis and characterization of 4-AMTT-Pd (II) complex over Fe3O4@SiO2 as supported nanocatalyst for Suzuki-Miyaura and Mizoroki-heck cross-coupling reactions in water. Appl Organomet Chem 32:e4171. https://doi.org/10.1002/aoc.4171

    Article  CAS  Google Scholar 

  5. Yousaf M, Zahoor AF, Akhtar R et al (2020) Development of green methodologies for Heck, Chan-Lam, Stille and Suzuki cross-coupling reactions. Mol Divers 24:821–839. https://doi.org/10.1007/s11030-019-09988-7

    Article  CAS  PubMed  Google Scholar 

  6. Byun S, Chung J, Kwon J, Moon Kim B (2015) Mechanistic studies of magnetically recyclable Pd-Fe3O4 heterodimeric nanocrystal-catalyzed organic reactions. Chem Asian J 10:982–988. https://doi.org/10.1002/asia.201403201

    Article  CAS  PubMed  Google Scholar 

  7. Begum T, Mondal M, Gogoi PK, Bora U (2015) Palladium-Schiff-base-silica framework as a robust and recyclable catalyst for Suzuki-Miyaura cross-coupling in aqueous media. RSC Adv 5:38085–38092. https://doi.org/10.1039/C5RA01574J

    Article  CAS  Google Scholar 

  8. Akbarzadeh P, Koukabi N, Kolvari E (2020) Polythiophene-functionalized magnetic carbon nanotube-supported copper (I) complex: a novel and retrievable heterogeneous catalyst for the “Phosphine-and Palladium-Free” Suzuki-Miyaura cross-coupling reaction. Mol Divers 24:1125–1137. https://doi.org/10.1007/s11030-019-10016-x

    Article  CAS  PubMed  Google Scholar 

  9. Sheykhan M, Yahyazadeh A, Rahemizadeh Z (2016) Cu–EDTA-modified APTMS-Fe3O4@SiO2 core–shell nanocatalyst: a novel magnetic recoverable catalyst for the Biginelli reaction. RSC Adv 6:34553–34563. https://doi.org/10.1039/C6RA02415G

    Article  CAS  Google Scholar 

  10. Duan X, Liu J, Hao J et al (2018) Magnetically recyclable nanocatalyst with synergetic catalytic effect and its application for 4-nitrophenol reduction and Suzuki coupling reactions. Carbon N Y 130:806–813. https://doi.org/10.1016/j.carbon.2018.01.038

    Article  CAS  Google Scholar 

  11. Zolfigol MA, Khazaei A, Alaie S et al (2016) Experimental and theoretical approving of anomeric based oxidation in the preparation of 2-sbstituted benz-(imida, oxa and othia)-zoles using [2,6-DMPy-NO2]C(NO2)3 as a novel nano molten salt catalyst. RSC Adv 6:58667–58679. https://doi.org/10.1039/C6RA13231F

    Article  CAS  Google Scholar 

  12. Hajipour AR, Tavangar-Rizi Z (2017) Methionine-functionalized chitosan–Pd(0) complex: a novel magnetically separable catalyst for Heck reaction of aryl iodides and aryl bromides at room temperature in water as only solvent. Appl Organomet Chem 31:e3638. https://doi.org/10.1002/aoc.3638

    Article  CAS  Google Scholar 

  13. Hadian-Dehkordi L, Hosseini-Monfared H (2016) Enantioselective aerobic oxidation of olefins by magnetite nanoparticles at room temperature: a chiral carboxylic acid strategy. Green Chem 18:497–550. https://doi.org/10.1039/C5GC01774B

    Article  CAS  Google Scholar 

  14. Rohani S, Mohammadi Ziarani G, Badiei A (2019) Pd embedded N, S co-doped graphene wrapped core-shell magnetic nanospheres: engineered stable nanocatalyst for Suzuki couplings. Appl Organomet Chem 33:e5142. https://doi.org/10.1002/aoc.5142

    Article  CAS  Google Scholar 

  15. Keypour H, Saremi SG, Noroozi M, Veisi H (2017) Synthesis of magnetically recyclable Fe3O4@[(EtO)3Si–L1H]/Pd (II) nanocatalyst and application in Suzuki and Heck coupling reactions. Appl Organomet Chem 31:e3558. https://doi.org/10.1002/aoc.3558

    Article  CAS  Google Scholar 

  16. Azad S, Mirjalili BBF (2019) One-pot solvent-free synthesis of 2,3-dihydro-2-substituted-1H-naphtho [1,2-e][1,3] oxazine derivatives using Fe3O4@nano-cellulose/TiCl as a bio-based and recyclable magnetic nano-catalyst. Mol Divers 23:413–420. https://doi.org/10.1007/s11030-018-9884-6

    Article  CAS  PubMed  Google Scholar 

  17. Ghorbani-Choghamarani A, Tahmasbi B, Moradi Z (2017) S-Benzylisothiourea complex of palladium on magnetic nanoparticles: a highly efficient and reusable nanocatalyst for synthesis of polyhydroquinolines and Suzuki reaction. Appl Organomet Chem 31:e3665. https://doi.org/10.1002/aoc.3665

    Article  CAS  Google Scholar 

  18. Dehkordi S, Jafari AA, Albadi J, Samimi HA (2022) Mesoporous epoxidized soybean oil-supported copper-based magnetic nanocatalyst and amberlite-supported azide as a green and efficient catalytic system for 1, 2, 3-triazole synthesis. Mol Divers 26:1–16. https://doi.org/10.1007/s11030-022-10408-6

    Article  CAS  Google Scholar 

  19. Ferdousian R, Behbahani FK, Mohtat B (2022) Synthesis and characterization of Fe3O4@Sal@Cu as a novel, efficient and heterogeneous catalyst and its application in the synthesis of 2-amino-4H-chromenes. Mol Divers 26:1–13

    Article  Google Scholar 

  20. Zhang L, Li P, Liu C et al (2014) A highly efficient and recyclable Fe3O4 magnetic nanoparticle immobilized palladium catalyst for the direct C-2 arylation of indoles with arylboronic acids. Catal Sci Technol 4:1979–1988. https://doi.org/10.1039/C4CY00040D

    Article  CAS  Google Scholar 

  21. Kandathil V, Fahlman BD, Sasidhar BS et al (2017) A convenient, efficient and reusable N-heterocyclic carbene-palladium (ii) based catalyst supported on magnetite for Suzuki-Miyaura and Mizoroki-Heck cross-coupling reactions. New J Chem 41:9531–9545. https://doi.org/10.1039/C7NJ01876B

    Article  CAS  Google Scholar 

  22. Han F, Xu Y, Zhu R et al (2018) Highly active NHC–Pd (ii) complexes for cross coupling of aryl chlorides and arylboronic acids: an investigation of the effect of remote bulky groups. New J Chem 42:7422–7427. https://doi.org/10.1039/C8NJ01047A

    Article  CAS  Google Scholar 

  23. Sharma KN, Satrawala N, Srivastava AK et al (2019) Palladium (ii) ligated with a selenated (Se, C NHC, N−)-type pincer ligand: an efficient catalyst for Mizoroki-Heck and Suzuki-Miyaura coupling in water. Org Biomol Chem 17:8969–8976. https://doi.org/10.1039/C9OB01674K

    Article  CAS  PubMed  Google Scholar 

  24. Nayan Sharma K, Satrawala N, Kumar Joshi R (2018) Thioether–NHC-ligated PdII complex for crafting a filtration-free magnetically retrievable catalyst for Suzuki-Miyaura coupling in water. Eur J Inorg Chem 2018:1743–1751. https://doi.org/10.1002/ejic.201800209

    Article  CAS  Google Scholar 

  25. Zhan J, Wu K, Yu X et al (2019) α-Fe2O3 nanoparticles decorated C@MoS2 nanosheet arrays with expanded spacing of (002) plane for ultrafast and high Li/Na-ion storage. Small 15:1901083. https://doi.org/10.1002/smll.201901083

    Article  CAS  Google Scholar 

  26. Veerakumar P, Thanasekaran P, Lu K-L et al (2017) Functionalized silica matrices and palladium: a versatile heterogeneous catalyst for Suzuki, Heck, and Sonogashira reactions. ACS Sustain Chem Eng 5:6357–6376. https://doi.org/10.1021/acssuschemeng.7b00921

    Article  CAS  Google Scholar 

  27. Karami K, Abedanzadeh S, Vahidnia O et al (2017) Orthopalladated complexes of phosphorus ylide: Poly (N-vinyl-2-pyrrolidone)-stabilized palladium nanoparticles as reusable heterogeneous catalyst for Suzuki and Heck cross-coupling reactions. Appl Organomet Chem 31:e3768. https://doi.org/10.1002/aoc.3768

    Article  CAS  Google Scholar 

  28. Sahu D, Silva AR, Das P (2016) Facile synthesis of palladium nanoparticles supported on silica: an efficient phosphine-free heterogeneous catalyst for Suzuki coupling in aqueous media. Catal Commun 86:32–35. https://doi.org/10.1016/j.catcom.2016.08.005

    Article  CAS  Google Scholar 

  29. Bai L, Wang J (2008) Reusable, polymer-supported, palladium-catalyzed, atom-efficient coupling reaction of aryl halides with sodium tetraphenylborate in water by focused microwave irradiation. Adv Synth Catal 350:315–320. https://doi.org/10.1002/adsc.200700361

    Article  CAS  Google Scholar 

  30. Eidi E, Kassaee MZ, Nasresfahani Z (2015) Nanocrystalline TiO2, via green combustion synthesis, as an efficient and reusable catalyst for the preparation of 1,8-dioxooctahydroxanthenes and 1,8-dioxodecahydroacridines. Appl Organomet Chem 29:793–797. https://doi.org/10.1002/aoc.3370

    Article  CAS  Google Scholar 

  31. Eidi E, Kassaee MZ, Nasresfahani Z (2016) Synthesis of 2,4,5-trisubstituted imidazoles over reusable CoFe2O4 nanoparticles: an efficient and green sonochemical process. Appl Organomet Chem 30:561–565. https://doi.org/10.1002/aoc.3470

    Article  CAS  Google Scholar 

  32. Nasresfahani Z, Kassaee MZ, Eidi E (2016) Homopiperazine sulfamic acid functionalized mesoporous silica nanoparticles (MSNs-HPZ-SO3H) as an efficient catalyst for one-pot synthesis of 1-amidoalkyl-2-naphthols. New J Chem 40:4720–4726. https://doi.org/10.1039/C5NJ02974K

    Article  CAS  Google Scholar 

  33. Nasresfahani Z, Kassaee MZ (2018) Cu (II) immobilized on mesoporous organosilica as an efficient and reusable nanocatalyst for one-pot Biginelli reaction under solvent-free conditions. Appl Organomet Chem 32:e4106. https://doi.org/10.1002/aoc.4106

    Article  CAS  Google Scholar 

  34. Fakhri A, Naghipour A (2018) Organometallic polymer-functionalized Fe 3 O 4 nanoparticles as a highly efficient and eco-friendly nanocatalyst for C-C bond formation. Transit Met Chem 43:463–472. https://doi.org/10.1007/s11243-018-0233-5

    Article  CAS  Google Scholar 

  35. Ghorbani-Choghamarani A, Rabiei H (2016) Synthesis, characterization, and application of palladium-dithizone immobilized on magnetic nanoparticles as an efficient and recoverable catalyst for Suzuki type coupling reactions. Tetrahedron Lett 57:159–162. https://doi.org/10.1016/j.tetlet.2015.11.096

    Article  CAS  Google Scholar 

  36. Cho S-D, Kim H-K, Yim H et al (2007) Suzuki-Miyaura coupling reaction of aryl chlorides using di (2, 6-dimethylmorpholino) phenylphosphine as ligand. Tetrahedron 63:1345–1352. https://doi.org/10.1016/j.tet.2006.12.001

    Article  CAS  Google Scholar 

  37. Jarret RM, Keil N, Allen S et al (1989) Friedel Crafts acylation and alkylation with acid chlorides. J Chem Educ 66:1056. https://doi.org/10.1021/ed066p1056

    Article  CAS  Google Scholar 

  38. Ghorbani-Choghamarani A, Tahmasbi B, Moradi P (2016) Synthesis of a new Pd (0)-complex supported on boehmite nanoparticles and study of its catalytic activity for Suzuki and Heck reactions in H 2 O or PEG. RSC Adv 6:43205–43216. https://doi.org/10.1039/C6RA02967A

    Article  CAS  Google Scholar 

  39. Alacid E, Najera C (2008) First cross-coupling reaction of potassium aryltrifluoroborates with organic chlorides in aqueous media catalyzed by an oxime-derived palladacycle. Org Lett 10:5011–5014. https://doi.org/10.1021/ol802024j

    Article  CAS  PubMed  Google Scholar 

  40. Beygzadeh M, Alizadeh A, Khodaei MM, Kordestani D (2013) Biguanide/Pd (OAc)2 immobilized on magnetic nanoparticle as a recyclable catalyst for the heterogeneous Suzuki reaction in aqueous media. Catal Commun 32:86–91. https://doi.org/10.1016/j.catcom.2012.11.028

    Article  CAS  Google Scholar 

  41. Lei L (2019) Pd–Schiff base complex supported on Fe3O4 magnetic nanoparticles: A new and highly efficient reusable catalyst for C-C bond formation in water. Appl Organomet Chem 33:e5158. https://doi.org/10.1002/aoc.5158

    Article  CAS  Google Scholar 

  42. Nikoorazm M, Ghorbani F, Ghorbani-Choghamarani A, Erfani Z (2018) Pd (0)-S-propyl-2-aminobenzothioate immobilized onto functionalized magnetic nanoporous MCM-41 as efficient and recyclable nanocatalyst for the Suzuki, Stille and Heck cross coupling reactions. Appl Organomet Chem 32:e4282. https://doi.org/10.1002/aoc.4282

    Article  CAS  Google Scholar 

  43. Eslahi H, Sardarian AR, Esmaeilpour M (2021) Green and sustainable palladium nanomagnetic catalyst stabilized by glucosamine-functionalized Fe3O4@SiO2 nanoparticles for Suzuki and Heck reactions. Appl Organomet Chem 35:e6260. https://doi.org/10.1002/aoc.6260

    Article  CAS  Google Scholar 

  44. Nikoorazm M, Ghorbani-Choghamarani A, Jabbari A (2016) A facile preparation of palladium Schiff base complex supported into MCM-41 mesoporous and its catalytic application in Suzuki and Heck reactions. J Porous Mater 23:967–975. https://doi.org/10.1007/s10934-016-0154-7

    Article  CAS  Google Scholar 

  45. Nasrollahzadeh M, Sajadi SM, Rostami-Vartooni A, Khalaj M (2015) Green synthesis of Pd/Fe3O4 nanoparticles using Euphorbia condylocarpa M. Bieb root extract and their catalytic applications as magnetically recoverable and stable recyclable catalysts for the phosphine-free Sonogashira and Suzuki coupling reactions. J Mol Catal A Chem 396:31–39. https://doi.org/10.1016/j.molcata.2014.09.029

    Article  CAS  Google Scholar 

  46. Elhampour A, Mirhosseyni MS, Nemati F (2018) Palladium nanoparticles supported on modified hollow Fe3O4@TiO2: Preparation, characterization, and catalytic activity in Suzuki cross-coupling reactions. J Chin Chem Soc 65:875–882. https://doi.org/10.1002/jccs.201700341

    Article  CAS  Google Scholar 

  47. Nouri K, Ghassemzadeh M, Mohsenzadeh F, Afsharpour M (2020) Pd (0) complex of fuberidazole modified magnetic nanoparticles: a novel magnetically retrievable high-performance catalyst for Suzuki and Stille C-C coupling reactions. Appl Organomet Chem 34:e5771. https://doi.org/10.1002/aoc.5771

    Article  CAS  Google Scholar 

  48. Chen T, Gao J, Shi M (2006) A novel tridentate NHC–Pd (II) complex and its application in the Suzuki and Heck-type cross-coupling reactions. Tetrahedron 62:6289–6294. https://doi.org/10.1016/j.tet.2006.04.034

    Article  CAS  Google Scholar 

  49. Khazaei A, Sarmasti N, Seyf JY (2018) Anchoring high density sulfonic acid based ionic liquid on the magnetic nano-magnetite (Fe3O4), application to the synthesis of hexahydroquinoline derivatives. J Mol Liq 262:484–494. https://doi.org/10.1016/j.molliq.2018.04.125

    Article  CAS  Google Scholar 

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  1. Department of Chemistry, Tarbiat Modares University, Tehran, Iran

    Sajad Mohammadian Souri, Esmaiel Eidi & Mohamad Zaman Kassaee

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Souri, S.M., Eidi, E. & Kassaee, M.Z. Efficient Suzuki coupling over novel magnetic nanoparticle: Fe3O4/L-(+)-tartaric acid/Pd(0). Mol Divers 27, 1469–1479 (2023). https://doi.org/10.1007/s11030-022-10507-4

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