Iron oxide-supported copper oxide nanoparticles (nanocat-Fe-CuO): Magnetically recyclable catalysts for the synthesis of pyrazole derivatives, 4-methoxyaniline, and ullmann-type condensation reactions

ACS Sustainable Chemistry and Engineering

Volumn 2, Issue 7, 2014, Pages 1699-1706

  Shelke, Sharad N ^a   Bankar, Swapnil R ^a   Mhaske, Ganesh R ^a   Kadam, Samadhan S ^a   Murade, Dinesh K ^a   Bhorkade, Shashikant B ^a   Rathi, Anuj K ^b   Bundaleski, Nenad ^c   Teodoro, Orlando M N D ^c   Zboril, Radek ^b   Varma, Rajender S ^d   Gawande, Manoj B ^b  

^a S S G M College   (India)

^b PALACKÝ UNIVERSITY   (Czech Republic)

^c UNIVERSIDADE NOVA DE LISBOA   (Portugal)

^d U S ENVIRONMENTAL PROTECTION AGENCY   (United States)

Author keywords

Benign media; Magnetite copper oxide; Pyrazole synthesis; Recyclable catalysts; Ullmann reaction

Indexed keywords

CATALYSTS; CONDENSATION REACTIONS; IRON COMPOUNDS; MAGNETITE; MAGNETITE NANOPARTICLES; NANOPARTICLES;

AQUEOUS MEDIUM; BENIGN MEDIA; COPPER OXIDE NANOPARTICLES; MAGNETICALLY SEPARABLE; PYRAZOLE DERIVATIVES; PYRAZOLES; RECYCLABLE CATALYST; ULLMANN REACTION;

SYNTHESIS (CHEMICAL);

EID: 84903945185     PISSN: None     EISSN: 21680485     Source Type: Journal    
DOI: 10.1021/sc500160f     Document Type: Conference Paper

References (60)

1. Astruc, D.; Lu, F.; Aranzaes, J. R. Nanoparticles as recyclable catalysts: The frontier between homogeneous and heterogeneous catalysis Angew. Chem., Int. Ed. 2005, 44 (48) 7852-7872
2. Gawande, M. B.; Pandey, R. K.; Jayaram, R. V. Role of mixed metal oxides in catalysis science-versatile applications in organic synthesis Catal. Sci. Technol. 2012, 2 (6) 1113-1125
3. Corma, A.; Garcia, H. Supported gold nanoparticles as catalysts for organic reactions Chem. Soc. Rev. 2008, 37 (9) 2096-2126
4. Climent, M. J.; Corma, A.; Iborra, S. Heterogeneous Catalysts for the One-Pot Synthesis of Chemicals and Fine Chemicals Chem. Rev. 2011, 111 (2) 1072-1133
5. Gawande, M. B.; Branco, P. S.; Parghi, K.; Shrikhande, J. J.; Pandey, R. K.; Ghumman, C. A. A.; Bundaleski, N.; Teodoro, O.; Jayaram, R. V. Synthesis and characterization of versatile MgO-ZrO2 mixed metal oxide nanoparticles and their applications Catal. Sci. Technol. 2011, 1 (9) 1653-1664
6. 2 nanoparticle-catalyzed O-tert-Boc protection of alcohols and phenols under solvent-free conditions Appl. Organomet. Chem. 2012, 26 (8) 395-400
7. Gawande, M. B.; Rathi, A.; Nogueira, I. D.; Ghumman, C. A. A.; Bundaleski, N.; Teodoro, O. M. N. D.; Branco, P. S. A Recyclable Ferrite-Co Magnetic Nanocatalyst for the Oxidation of Alcohols to Carbonyl Compounds ChemPlusChem. 2012, 2012 (77) 865-871
8. Kim, S. B.; Pike, R. D.; Sweigart, D. A. Multifunctionality of Organometallic Quinonoid Metal Complexes: Surface Chemistry, Coordination Polymers, and Catalysts Acc. Chem. Res. 2013, 46 (11) 2485-2497
9. Lu, J.; Toy, P. H. Organic Polymer Supports for Synthesis and for Reagent and Catalyst Immobilization Chem. Rev. 2009, 109 (2) 815-838
10. Guo, H.; Liu, X.; Xie, Q.; Wang, L.; Peng, D.-L.; Branco, P. S.; Gawande, M. B. Disproportionation route to monodispersed copper nanoparticles for the catalytic synthesis of propargylamines Rsc. Adv. 2013, 3 (43) 19812-19815
11. Suzuta, T.; Toba, M.; Abe, Y.; Yoshimura, Y. Iron Oxide Catalysts Supported on Porous Silica for the Production of Biodiesel from Crude Jatropha Oil J. Am. Oil Chem. Soc. 2012, 89 (11) 1981-1989
12. Kale, S. R.; Kahandal, S. S.; Gawande, M. B.; Jayaram, R. V. Magnetically recyclable [gamma]-Fe2O3-HAP nanoparticles for the cycloaddition reaction of alkynes, halides and azides in aqueous media Rsc. Adv. 2013, 3 (22) 8184-8192
13. 4) as a support for recyclable catalysts in the development of sustainable methodologies Chem. Soc. Rev. 2013, 42 (8) 3371-3393
14. Baig, R. B. N.; Varma, R. S. A highly active and magnetically retrievable nanoferrite-DOPA-copper catalyst for the coupling of thiophenols with aryl halides Chem. Commun. 2012, 48 (20) 2582-2584
15. Vaddula, B. R.; Saha, A.; Leazer, J.; Varma, R. S. A simple and facile Heck-type arylation of alkenes with diaryliodonium salts using magnetically recoverable Pd-catalyst Green Chem. 2012, 14 (8) 2133-2136
16. Rezaeifard, A.; Jafarpour, M.; Farshid, P.; Naeimi, A. Nanomagnet-Supported Partially Brominated Manganese-Porphyrin as a Promising Catalyst for the Selective Heterogeneous Oxidation of Hydrocarbons and Sulfides in Water Eur. J. Inorg. Chem. 2012, 33, 5515-5524
17. 4)-Supported Phosphomolybdate as an Efficient, Green, Recyclable Catalyst for Synthesis of ?-Hydroxy Hydroperoxides Adv. Synth. Catal. 2013, 355 (14-15) 2952-2959
18. Aliaga, M. J.; Ramon, D. J.; Yus, M. Impregnated copper on magnetite: an efficient and green catalyst for the multicomponent preparation of propargylamines under solvent free conditions Org. Biomol. Chem. 2010, 8 (1) 43-46
19. Liu, J. M.; Peng, X. G.; Sun, W.; Zhao, Y. W.; Xia, C. G. Magnetically separable Pd catalyst for carbonylative Sonogashira coupling reactions for the synthesis of alpha,?-alkynyl ketones Org. Lett. 2008, 10 (18) 3933-3936
20. 4/Pd nanoparticles Angew. Chem., Int. Ed. 2010, 49 (42) 7786-7789
21. Sharghi, H.; Khalifeh, R.; Doroodmand, M. M. Copper nanoparticles on charcoal for multicomponent catalytic synthesis of 1,2,3-triazole derivatives from benzyl halides or alkyl halides, terminal alkynes and sodium azide in water as a ?green? solvent Adv. Synth. Catal. 2009, 351 (1 + 2) 207-218
22. Alonso, F.; Moglie, Y.; Radivoy, G.; Yus, M. Multicomponent synthesis of 1,2,3-triazoles in water catalyzed by copper nanoparticles on activated carbon Adv. Synth. Catal. 2010, 352 (18) 3208-3214
23. Ranu, B. C.; Dey, R.; Chatterjee, T.; Ahammed, S. Copper nanoparticle-catalyzed carbon-carbon and carbon-heteroatom bond formation with a greener perspective ChemSusChem. 2012, 5 (1) 22-44
24. Alonso, F.; Moglie, Y.; Radivoy, G.; Yus, M. Multicomponent Click Synthesis of 1,2,3-Triazoles from Epoxides in Water Catalyzed by Copper Nanoparticles on Activated Carbon J. Org. Chem. 2011, 76 (20) 8394-8405
25. Mitsudome, T.; Mikami, Y.; Ebata, K.; Mizugaki, T.; Jitsukawa, K.; Kaneda, K. Copper nanoparticles on hydrotalcite as a heterogeneous catalyst for oxidant-free dehydrogenation of alcohols Chem. Commun. 2008, 39, 4804-4806
26. 2O acting as a robust catalyst in Cu AAC reactions: water is the required medium Green Chem. 2011, 13 (3) 562-565
27. Alonso, F.; Moglie, Y.; Radivoy, G.; Yus, M. Copper-Catalyzed Multicomponent Click Synthesis of 5-Alkynyl 1,2,3-Triazoles under Ambient Conditions Synlett. 2012, 15, 2179-2182
28. Strassberger, Z.; Alberts, A. H.; Louwerse, M. J.; Tanase, S.; Rothenberg, G. Catalytic cleavage of lignin [small beta]-O-4 link mimics using copper on alumina and magnesia-alumina Green Chem. 2013, 15 (3) 768-774
29. 2O@Cu with high activity for the Sonogashira coupling reaction Chem. Commun. 2012, 48 (47) 5862-5864
30. Ranu, B. C.; Dey, R.; Chatterjee, T.; Ahammed, S. Copper Nanoparticle-Catalyzed Carbon-Carbon and Carbon-Heteroatom Bond Formation with a Greener Perspective ChemSusChem. 2012, 5 (1) 22-44
31. Boettcher, S. W.; Spurgeon, J. M.; Putnam, M. C.; Warren, E. L.; Turner-Evans, D. B.; Kelzenberg, M. D.; Maiolo, J. R.; Atwater, H. A.; Lewis, N. S. Energy-Conversion Properties of Vapor-Liquid-Solid-Grown Silicon Wire-Array Photocath. Sci. 2010, 327 (5962) 185-187
32. Takagi, D.; Homma, Y.; Hibino, H.; Suzuki, S.; Kobayashi, Y. Single-walled carbon nanotube growth from highly activated metal nanoparticles Nano Lett. 2006, 6 (12) 2642-2645
33. Vitulli, G.; Bernini, M.; Bertozzi, S.; Pitzalis, E.; Salvadori, P.; Coluccia, S.; Martra, G. Nanoscale Copper Particles Derived from Solvated Cu Atoms in the Activation of Molecular Oxygen. Chem. Mater. 2002, 14 (3) 1183-1186
34. Kamal, A.; Srinivasulu, V.; Murty, J. N. S. R. C.; Shankaraiah, N.; Nagesh, N.; Srinivasa Reddy, T.; Subba Rao, A. V. Copper Oxide Nanoparticles Supported on Graphene Oxide-Catalyzed S-Arylation: An Efficient and Ligand-Free Synthesis of Aryl Sulfides Adv. Synth. Catal. 2013, 355 (11-12) 2297-2307
35. 4 Nanoparticles as an Efficient Catalyst for C-O Cross-Coupling of Phenols with Aryl Halides ChemCatChem. 2011, 3 (1) 146-149
36. 4 as a magnetically separable and reusable catalyst for the synthesis of diaryl/aryl alkyl sulfides via cross-coupling process under ligand-free conditions Org. Biomol. Chem. 2011, 9 (17) 5989-5996
37. Swapna, K.; Murthy, S. N.; Nageswar, Y. V. D. Magnetically Separable and Reusable Copper Ferrite Nanoparticles for Cross-Coupling of Aryl Halides with Diphenyl Diselenide Eur. J. Org. Chem. 2011, 10, 1940-1946
38. 4 Nanoparticles as Magnetically Recoverable and Reusable Catalyst for Azide-Alkyne Click Condensation Heterocycles 2012, 86 (2) 1023-1030
39. 4 nano particles catalyzed multicomponent synthesis of 1,4-disubstituted 1,2,3-triazoles in tap water using click chemistry Tetrahedron Lett. 2012, 53 (34) 4595-4599
40. 4 Nanoparticles as Highly Active Catalysts for Csp(3)-Csp and Csp(3)-Csp(3) Oxidative Cross-Dehydrogenative Coupling Synlett 2013, 24 (13) 1637-1642
41. Hudson, R.; Li, C. J.; Moores, A. Magnetic copper-iron nanoparticles as simple heterogeneous catalysts for the azide-alkyne click reaction in water Green Chem. 2012, 14 (3) 622-624
42. Kantam, M. L.; Yadav, J.; Laha, S.; Jha, S. Synthesis of Propargylamines by Three-Component Coupling of Aldehydes, Amines and Alkynes Catalyzed by Magnetically Separable Copper Ferrite Nanoparticles Synlett 2009, 11, 1791-1794
43. Kasi Viswanath, I. V.; Murthy, Y. L. N. One-Pot, Three-Component Synthesis of 1, 4-Dihydropyridines by Using Nano Crystalline Copper Ferrite Chem. Sci. Trans. 2013, 2 (1) 227-233
44. Senapati, K. M.; Phukan, P. Magnetically separable cobalt ferrite nanocatalyst for aldol condensations of aldehydes and ketones Bull. Catal. Soc. Indian 2011, 9, 1-8
45. 4-immobilized domino Knoevenagel condensation, Michael addition, and cyclization catalyst Catal. Commun. 2013, 37, 69-74
46. Banon-Caballero, A.; Guillena, G.; Najera, C.; Faggi, E.; Sebastian, R. M.; Vallribera, A. Recoverable silica-gel supported binam-prolinamides as organocatalysts for the enantioselective solvent-free intra-and intermolecular aldol reaction Tetrahedron 2013, 69 (4) 1307-1315
47. Kandel, K.; Althaus, S. M.; Peeraphatdit, C.; Kobayashi, T.; Trewyn, B. G.; Pruski, M. Slowing, II. Substrate inhibition in the heterogeneous catalyzed aldol condensation: A mechanistic study of supported organocatalysts J. Catal. 2012, 291, 63-68
48. Bekhit, A. A.; Fahmy, H. T. Y.; Rostom, S. A. F.; Bekhit, A. E.-D. A. Synthesis and biological evaluation of some thiazolylpyrazole derivatives as dual anti-inflammatory antimicrobial agents Eur. J. Med. Chem. 2010, 45 (12) 6027-6038
49. Bekhit, A. A.; Hymete, A.; Bekhit, A. E.-D. A.; Damtew, A.; Aboul-Enein, H. Y. Pyrazoles as Promising Scaffold for the Synthesis of Anti-Inflammatory and/or Antimicrobial Agent: A Review Mini-Rev. Med. Chem. 2010, 10 (11) 1014-1033
50. Vijesh, A. M.; Isloor, A. M.; Shetty, P.; Sundershan, S.; Fun, H. K. New pyrazole derivatives containing 1,2,4-triazoles and benzoxazoles as potent antimicrobial and analgesic agents Eur. J. Med. Chem. 2013, 62, 410-415
51. Gawande, M. B.; Bonifacio, V. D. B.; Luque, R.; Branco, P. S.; Varma, R. S. Benign by design: catalyst-free in-water, on-water green chemical methodologies in organic synthesis Chem. Soc. Rev. 2013, 42 (12) 5522-5551
52. Gawande, M. B.; Rathi, A. K.; Nogueira, I. D.; Varma, R. S.; Branco, P. S. Magnetite-supported sulfonic acid: a retrievable nanocatalyst for the Ritter reaction and multicomponent reactions Green Chem. 2013, 15 (7) 1895-1899
53. Gawande, M. B.; Bonifácio, V. D. B.; Luque, R.; Branco, P. S.; Varma, R. S. Solvent-Free and Catalysts-Free Chemistry: A Benign Pathway to Sustainability ChemSusChem. 2014, 7 (1) 24-44
54. Gawande, M. B.; Shelke, S. N.; Zboril, R.; Varma, R. S. Microwave-Assisted Chemistry: Synthetic Applications for Rapid Assembly of Nanomaterials and Organics Acc. Chem. Res. 2014, 47 (4) 1338-1348
55. Gawande, M. B.; Bonifacio, V. D. B.; Varma, R. S.; Nogueira, I. D.; Bundaleski, N.; Ghumman, C. A. A.; Teodoro, O. M. N. D.; Branco, P. S. Magnetically recyclable magnetite-ceria (Nanocat-Fe-Ce) nanocatalyst- applications in multicomponent reactions under benign conditions Green Chem. 2013, 15, 1226-1231
56. Biesinger, M. C.; Lau, L. W. M.; Gerson, A. R.; Smart, R. S. C. Resolving surface chemical states in XPS analysis of first row transition metals, oxides and hydroxides: Sc, Ti, V, Cu and Zn Appl. Surf. Sci. 2010, 257 (3) 887-898
57. 2 receptor ligands Bioorg. Med. Chem. 2003, 11 (22) 4807-4813
58. Chornous, V. A.; Bratenko, M. K.; Vovk, M. V. Synthesis of 1-aryl-4-formylpyrazoles from acetaldehyde N-aryl-hydrazones by the Vilsmeier-Haack method Chem. Heterocycl. Compnd. 2006, 42 (9) 1242-1243
59. Teodoro, O.; Silva, J.; Moutinho, A. M. C. Multitechnique Surface-Analysis System-Apparatus Description Vacuum 1995, 46 (8-10) 1205-1209
60. Payne, B. P.; Biesinger, M. C.; McIntyre, N. S. X-ray photoelectron spectroscopy studies of reactions on chromium metal and chromium oxide surfaces J. Elect. Spec. Rel. Phenom. 2011, 184 (1-2) 29-37