Copper nanoparticles supported on agarose as a bioorganic and degradable polymer for multicomponent click synthesis of 1,2,3-triazoles under low copper loading in water

ACS Sustainable Chemistry and Engineering

Volumn 2, Issue 12, 2014, Pages 2658-2665

  Gholinejad, Mohammad ^a   Jeddi, Neda ^a  

^a INSTITUTE FOR ADVANCED STUDIES IN BASIC SCIENCES IASBS   (Iran)

Author keywords

Agarose; Click; Copper nanoparticles; Triazoles; Water

Indexed keywords

CATALYST ACTIVITY; CATALYSTS; COPPER; GAS ADSORPTION; METAL NANOPARTICLES; NANOPARTICLES; WATER;

AGAROSE; CHEMICAL REDUCTION; CLICK; COPPER NANOPARTICLES; DEGRADABLE POLYMERS; MILD REACTION CONDITIONS; NITROGEN ADSORPTION DESORPTION; TRIAZOLES;

SYNTHESIS (CHEMICAL);

EID: 84928472627     PISSN: None     EISSN: 21680485     Source Type: Journal    
DOI: 10.1021/sc500395b     Document Type: Article

References (55)

1. Alvarez, R.; Velazquez, S.; San-felix, A.; Aquaro, S.; De Clercq, E.; Perno, C-F.; Karlsson, A.; Balzarini, J.; Camarasa, M. J. 1, 2, 3-Triazole- [2′, 5′-bis-O- (tert-butyldimethylsilyl)-beta-D-ribofuranosyl]-3′-spiro- 5″- (4″-amino-1″, 2″-oxathiole 2″, 2″-dioxide) (TSAO) analogues: Synthesis and anti-HIV-1 activity. J. Med. Chem. 1994, 37, 4185-4194.
2. Velazquez, S.; Alvarez, R.; Perez, C.; Gago, F.; De Clercq, C.; Balzarini, J.; Camarasa, M. J. Regiospecific synthesis and anti-human immuno-deficiency virus activity of novel 5-substituted N-alkylcarbamoyl and N, N-dialkyl carbamoyl 1, 2, 3-triazole-TSAO analogues antihuman. Antiviral Chem. Chemother. 1998, 9, 481-489.
3. Genin, M. J.; Allwine, D. A.; Anderson, D. J.; Barbachyn, M. R.; Emmert, D. E.; Garmon, S. A.; Graber, D. R.; Grega, K. C.; Hester, J. B.; Hutchinson, D. K.; Morris, J.; Reischer, R. J.; Ford, C. W.; Zurenko, G. E.; Hamel, J. C.; Schaadt, R. D.; Stapert, D.; Yagi, B. H. Substituent effects on the antibacterial activity of nitrogen-carbon-linked (azolylphenyl)oxazolidinones with expanded activity against the fastidious gram-negative organisms Haemophilus influenzae and Moraxella catarrhalis. J. Med. Chem. 2000, 43, 953-970.
4. Brockunier, L. L.; Parmee, E. R.; Ok, H. O.; Candelore, M. R.; Cascieri, M. A.; Colwell, L. F.; Deng, L.; Feeney, W. P.; Forrest, M. J.; Hom, G. J.; MacIntyre, D. E.; Tota, L.; Wyvratt, M. J.; Fisher, M. H.; Weber, A. E. Human β3-adrenergic receptor agonists containing 1, 2, 3- Triazole-substituted benzenesulfonamides. Bioorg. Med. Chem. Lett. 2000, 10, 2111-2114.
5. Fan, W.-Q.; Katritzky, A. R. 1, 2, 3-Triazoles. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Elsevier Science: Oxford, U.K., 1996; Vol. 4, pp 1-126.
6. Huisgen, R. Kinetics and reaction mechanisms: Selected examples from the experience of forty years. Pure Appl. Chem. 1989, 61, 613-628.
7. Tornøe, C. W.; Christensen, C.; Meldal, M. Peptidotriazoles on solid phase: [1, 2, 3]-Triazoles by regiospecific copper (I)-catalyzed 1, 3- dipolar cycloadditions of terminal alkynes to azides. J. Org. Chem. 2002, 67, 3057-3064.
8. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. A stepwise Huisgen cycloaddition process: Copper (I)-catalyzed regioselective "ligation" of azides and terminal alkynes. Angew. Chem., Int. Ed. 2002, 41, 2596-2599.
9. Anastas, P. T.; Kirchhoff, M. M. Origins, current status, and future challenges of green chemistry. Acc. Chem. Res. 2002, 35, 686-693.
10. Anastas, P. T.; Eghbali, N. Green chemistry: Principles and practice. Chem. Soc. Rev. 2010, 39, 301-312.
11. Sheldon, R. A. The E Factor: Fifteen years on. Chem. Technol. 1994, 24, 38-47.
12. Liang, L.; Astruc, D. The copper (I)-catalyzed alkyne-azide cycloaddition (CuAAC) "click" reaction and its applications. Coord. Chem. Rev. 2011, 255, 2933-2945.
13. Meldal, M.; Tornøe, C.-W. Cu-catalyzed azide-alkyne cycloaddition. Chem. Rev. 2008, 108, 2952-3015.
14. Harmand, L.; Lescure, M.-H.; Candelon, N.; Duttine, M.; Lastécouères, D.; Vincent, J.-M. Huisgen click cycloadditions from a copper (II)-tren precatalyst without external sacrificial reductant. Tetrahedron Lett. 2012, 53, 1417-1420.
15. Dervaux, B.; Du Prez, F. E. Heterogeneous azide-alkyne click chemistry: Towards metal-free end Products. Chem. Sci. 2012, 3, 959- 966.
16. Jin, T.; Yan, M.; Yamamoto, Y. Click chemistry of alkyne-azide cycloaddition using nanostructured copper catalysts. Chem Cat Chem. 2012, 4, 1217-1229.
17. Lal, S.; McNally, J.; White, A. J. P.; Dieź-Gonzaléz, S. Novel phosphinite and phosphonite copper (I) complexes: Efficient catalysts for click azide-alkyne cycloaddition reactions. Organometallics 2011, 30, 6225-6232.
18. Nakamura, T.; Terashima, T.; Ogata, K.; Fukuzawa, S.-I. Copper (I) 1, 2, 3-triazol-5-ylidene complexes as efficient catalysts for click reactions of azides with alkynes. Org. Lett. 2011, 13, 620-623.
19. Cano, I.; Nicasio, M. C.; Perez, P. J. Copper (I) complexes as catalysts for the synthesis of N-sulfonyl-1, 2, 3-triazoles from Nsulfonylazides and alkynes. Org. Biomol. Chem. 2010, 8, 536-538.
20. Pathigoolla, A.; Pola, R. P.; Sureshan, K. M. A versatile solventfree azide-alkyne click reaction catalyzed by in situ generated copper nanoparticles. Appl. Catal., A 2013, 453, 151-158.
21. Alonso, F.; Moglie, Y.; Radivoy, G.; Yus, M. Copper nanoparticles in click chemistry: An alternative catalytic system for the cycloaddition of terminal alkynes and azides. Tetrahedron Lett. 2009, 50, 2358-2362.
22. Veerakumar, P.; Velayudham, M.; Lu, K.-L.; Rajagopal, S. Highly dispersed silica-supported nanocopper as an efficient heterogeneous catalyst: Application in the synthesis of 1, 2, 3-triazoles and thioethers. Catal. Sci. Technol. 2011, 1, 1512-1525.
23. 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, 622-624.
24. Kaboudin, B.; Mostafalu, R.; Yokomatsu, T. Fe3O4 nanoparticlesupported Cu (II)-β-cyclodextrin complex as a magnetically recoverable and reusable catalyst for the synthesis of symmetrical biaryls and 1, 2, 3- Triazoles from aryl boronic acids. Green Chem. 2013, 15, 2266-2274.
25. Lee, B. S.; Yi, M.; Chu, S. Y.; Lee, J. Y.; Kwon, H. R.; Lee, K. R.; Kang, D.; Kim, W. S.; Lim, H. B.; Lee, J.; Youn, H.-J.; Chi, D. Y.; Hur, N. H. Copper nitride nanoparticles supported on a superparamagnetic mesoporous microsphere for toxic-free click chemistry. Chem. Commun. 2010, 46, 3935-3937.
26. Wang, L.; Cai, C. Reusable polymer-supported copper catalyst for one-pot synthesis of 1-alkyl- And 1-aryl-1, 2, 3-triazoles: Green, simple, and effective. Green Chem. Lett. Rev. 2010, 3, 121-125.
27. Zhang, Z.; Dong, C.; Yang, C.; Hu, D.; Long, J.; Wang, L.; Li, H.; Chen, Y.; Kong, D. Stabilized copper (I) oxide nanoparticles catalyze azide-alkyne click reactions in water. Adv. Synth. Catal. 2010, 352, 1600-1604.
28. Sarkar, A.; Mukherjee, T.; Kapoor, S. PVP-stabilized copper nanoparticles: A reusable catalyst for "click" reaction between terminal alkynes and azides in nonaqueous solvents. J. Phys. Chem. C 2008, 112, 3334-3340.
29. 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, 8394- 8405.
30. Alonso, F.; Moglie, Y.; Radivoy, G.; Yus, M. Click chemistry from organic halides, diazonium salts and anilines in water catalysed by copper nanoparticles on activated carbon. Org. Biomol. Chem. 2011, 9, 6385-6395.
31. 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, 3208-3214.
32. Alonso, F.; Moglie, Y.; Radivoy, Y.; Yus, M. Alkenes as azido precursors for the one-pot synthesis of 1, 2, 3-triazoles catalyzed by copper nanoparticles on activated carbon. J. Org. Chem. 2013, 78, 5031- 5037.
33. Alonso, F.; Moglie, Y.; Radivoy, G.; Yus, M. Multicomponent click synthesis of potentially biologically active triazoles catalysed by copper nanoparticles on activated carbon in water. Heterocycles 2012, 84, 1033-1044.
34. 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, 207-218.
35. Lipshutz, B. H.; Taft, B. R. Heterogeneous copper-in-charcoalcatalyzed click chemistry. Angew. Chem., Int. Ed. 2006, 45, 8235-8238.
36. Jing, J.; Chen, G.; Li, W.; Xie, J.; Zhang, M. Surfactant-assisted hydrothermal synthesis and characterization of copper nano/microstructures and their application as catalysts in click chemistry. Mater. Lett. 2014, 115, 180-183.
37. Lipshutz, B. H.; Nihan, D. M.; Vinogradova, E.; Taft, B. R.; Bošković, Ž. V. Copper + nickel-in-charcoal (Cu-Ni/C): A bimetallic, heterogeneous catalyst for cross-couplings. Org. Lett. 2008, 10, 4279- 4282.
38. Song, Y.-J.; Yoo, C.-Y.; Hong, J.-T.; Kim, S.-J.; Son, S.-U.; Jang, H.- Y. Nanocrystalline copper oxide (II)-catalyzed alkyne-azide cycloadditions. Bull. Korean Chem. Soc. 2008, 29, 1561-1564.
39. Kim, J. Y.; Park, J. C.; Kang, H.; Song, H.; Park, K. H. CuO hollow nanostructures catalyze [3 + 2] cycloaddition of azides with terminal alkynes. Chem. Commun. 2010, 46, 439-441.
40. Roy, S.; Chatterjee, T.; Pramanik, M.; Singha, A.; Bhaumik, R. A.; Islam, M. Cu (II)-anchored functionalized mesoporous SBA-15: An efficient and recyclable catalyst for the one-pot Click reaction in water. J. Mol. Catal. A: Chem. 2014, 386, 78-85.
41. Soltani Rad, M. N.; Behrouz, S.; Movahedian, A.; Doroodmand, M. M.; Ghasemi, Y.; Rasoul-Amini, S.; Gandomani, A-R. A.; Rezaie, R. Doped nano-sized copper (I) oxide (Cu2O) on melamine[BOND] formaldehyde resin: A highly efficient heterogeneous nano catalyst for 'click' synthesis of some novel 1H-1, 2, 3-triazole derivatives having antibacterial activity. Helv. Chim. Acta 2013, 96, 688-701.
42. Chtchigrovsky, M.; Primo, A.; Gonzalez, P.; Molvinger, K.; Robitzer, M.; Quignard, F.; Taran, F. Functionalized chitosan as a green, recyclable, biopolymer-supported catalyst for the [3 + 2] Huisgen cycloaddition. Angew. Chem., Int. Ed. 2009, 48, 5916-5920.
43. Tokarek, K.; Hueso, J. L.; Kustrowski, P.; Stochel, G.; Kyzioł, A. Green synthesis of chitosan-stabilized copper nanoparticles. Eur. J. Inorg. Chem. 2013, 4940-4947.
44. Nasir Baig, R. B.; Vaddula, B. R.; Gonzalez, M. A.; Varma, R. S. NAllylation of amines with allyl acetates using chitosan-immobilized palladium. RSC Adv. 2014, 4, 9103-9106.
45. Dabbawala, A. A.; Sudheesh, N.; Bajaj, H. C. Palladium supported on chitosan as a recyclable and selective catalyst for the synthesis of 2- phenyl ethanol. Dalton Trans. 2012, 41, 2910-2917.
46. Cui, Y.; Zhang, L.; Li, Y. Synthesis of chitosan derivatives supported palladium complexes and their catalytic behavior in the Heck reaction. Polym. Adv. Technol. 2005, 16, 633-637.
47. Datta, K. K.; Srinivasan, B.; Eswaramoorthy, M. Synthesis of agarose-metal/semiconductor nanoparticles having superior bacteriocidal activity and their simple conversion to metal-carbon composites. J. Chem. Sci. 2008, 120, 579-586.
48. Firouzabadi, H.; Iranpoor, N.; Gholinejad, M.; Kazemi, F. Agarose hydrogel as an effective bioorganic ligand and support for the stabilization of palladium nanoparticles. Application as a recyclable catalyst for Suzuki-Miyaura reaction in aqueous media. RSC Adv. 2011, 1, 1013-1019.
49. Firouzabadi, H.; Iranpoor, N.; Kazemi, F.; Gholinejad, M. Palladium nano-particles supported on agarose as efficient catalyst and bioorganic ligand for C-C bond formation via solventless Mizoroki- Heck reaction and Sonogashira-Hagihara reaction in polyethylene glycol (PEG 400). J. Mol. Catal. A: Chem. 2012, 357, 154-161.
50. Gholinejad, M. Palladium nanoparticles supported on agarosecatalyzed Heck-Matsuda and Suzuki-Miyaura coupling reactions using aryl diazonium salts. Appl. Organomet. Chem. 2013, 27, 19-22.
51. Nasir Baig, R. B.; Varma, R. S. Copper on chitosan: A recyclable heterogeneous catalyst for azide-alkyne cycloaddition reactions in water. Green Chem. 2013, 15, 1839-1843.
52. Suyal, G.; Mennig, M.; Schmidt, H. Sol-gel synthesis of cuprous halide nanoparticles in a glassy matrix and their characterization. J. Mater. Chem. 2003, 13, 1783-1788.
53. Rouquerol, F. Rouquerol, J. Sing, K. Adsorption by Powders and Porous Solids; Academic Press: London, 1999.
54. Das, J.; Patil, S. N.; Awasthi, R.; Narasimhulu, C. P.; Trehan, S. An easy access to aryl azides from aryl amines under neutral conditions. Synthesis 2005, 1801-1806.
55. Orgueira, H. A.; Fokas, D.; Isome, Y.; Chan, P. C.-M.; Baldino, C. M. Regioselective synthesis of [1, 2, 3]-triazoles catalyzed by Cu (I) generated in situ from Cu (0) nanosize activated powder and amine hydrochloride salts. Tetrahedron Lett. 2005, 46, 2911-2914.