Nanoporous titania-supported gold nanoparticle-catalyzed green synthesis of 1,2,3-triazoles in aqueous medium

ACS Sustainable Chemistry and Engineering

Volumn 1, Issue 11, 2013, Pages 1405-1411

  Boominathan, Muthusamy ^a   Pugazhenthiran, Nalenthiran ^a   Nagaraj, Muthupandi ^a   Muthusubramanian, Shanmugam ^a   Murugesan, Sepperumal ^a   Bhuvanesh, Nattamai ^b  

^a MADURAI KAMARAJ UNIVERSITY   (India)

^b TEXAS A AND M UNIVERSITY   (United States)

Author keywords

Cycloaddition; Gold nanoparticles; Heterogeneous catalysis; Huisgen reaction; Triazole

Indexed keywords

1 ,3-DIPOLARCYCLOADDITION; BET ADSORPTION ISOTHERMS; DEPOSITION PRECIPITATION METHODS; GOLD NANOPARTICLES; HUISGEN REACTION; SPECTRAL TECHNIQUES; TRIAZOLE; TRIAZOLE DERIVATIVES;

CATALYSIS; CYCLOADDITION; GOLD; METAL NANOPARTICLES; NITROGEN COMPOUNDS; PRECIPITATION (CHEMICAL); TITANIUM DIOXIDE;

SYNTHESIS (CHEMICAL);

EID: 84887266363     PISSN: None     EISSN: 21680485     Source Type: Journal    
DOI: 10.1021/sc400147r     Document Type: Article

References (54)

1. Polshettiwar, V.; Varma, R. S. Green chemistry by nano-catalysis Green Chem. 2010, 12, 743-754
2. Rao, C. N. R.; Muller, A.; Cheetham, A. K. Nanomaterials Chemistry: Recent Developments and New Directions; Wiley-VCH: Weinheim, Germany, 2007; ISBN: 3527316647.
3. Laurent, S.; Forge, D.; Port, M.; Roch, A.; Robic, C.; Elst, L. V.; Muller, R. N. Magnetic iron oxide nanoparticles: Synthesis, stabilization, vectorization, physicochemical characterizations, and biological applications Chem. Rev. 2008, 108, 2064-2110
4. Burda, C.; Chen, Z.; Narayanan, R.; El-sayed, M. A. Chemistry and properties of nanocrystals of different shapes Chem. Rev. 2005, 105, 1025-1102
5. Narayanan, R.; El-Sayed, M. A. Catalysis with transition metal nanoparticles in colloidal solution: Nanoparticle shape dependence and stability J. Phys. Chem. B. 2005, 109, 12663-12676
6. Coperet, C.; Chabanas, M.; Saint-Arroman, R. P.; Basset, J. M. Homogeneous and heterogeneous catalysis: Bridging the gap through surface organometallic chemistry Angew. Chem., Int. Ed. 2003, 42, 156-181
7. Basset, J. M.; Choplin, A. Surface organometallic chemistry: A new approach to heterogeneous Catalysis ? J. Mol. Catal. 1993, 21, 95-108
8. Mizuno, N.; Misono, M. Heterogeneous catalysis Chem. Rev. 1998, 98, 199-218
9. Polshettiwar, V.; Len, C.; Fihri, A. Silica-supported palladium: Sustainable catalysts for cross-coupling reactions Coord. Chem. Rev. 2009, 253, 2599-2626
10. 3 J. Am. Chem. Soc. 2009, 131, 1775-1779
11. Polshettiwar, V.; Baruwati, B.; Varma, R. S. Nanoparticle-supported and magnetically recoverable nickel catalyst: A robust and economic hydrogenation and transfer hydrogenation protocol Green Chem. 2009, 11, 127-131
12. 3] for azide-alkyne cycloaddition reactions under strict click conditions J. Org. Chem. 2011, 76, 2367-2373
13. I-mediated azide-alkyne cycloaddition J. Org. Chem. 2009, 74, 2964-2974
14. Luo, S.; Xu, H.; Mi, X.; Li, J.; Zheng, X.; Cheng, J.-P. Evolution of pyrrolidine-type asymmetric organocatalysts by "click" chemistry J. Org. Chem. 2006, 71, 9244-9247
15. Nahrwold, M.; Bogner, T.; Eissler, S.; Verma, S.; Sewald, N. Clicktophycin-52": A bioactive cryptophycin-52 triazole analogue Org. Lett. 2010, 12, 1064-1067
16. Shetti, V. S.; Ravikanth, M. Synthesis of triazole-bridged unsymmetrical porphyrin dyads and porphyrin-ferrocene conjugates Eur. J. Org. Chem. 2010, 494-508
17. Kwok, S. W.; Fotsing, J. R.; Fraser, R. J.; Rodionov, V. O.; Fokin, V. V. Transition-metal-free catalytic synthesis of 1,5-diaryl-1,2,3-triazoles Org. Lett. 2010, 12, 4217-4219
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. Liu, M.; Reiser, O. A copper(I) isonitrile complex as a heterogeneous catalyst for azide-alkyne cycloaddition in water Org. Lett. 2011, 13, 1102-1105
20. Ozcubukcu, S.; Ozkal, E.; Jimeno, C.; Pericas, M. A. A highly active catalyst for Huisgen 1,3-dipolar cycloadditions based on the tris(triazolyl)methanol-Cu(I) structure Org. Lett. 2009, 11, 4680-4683
21. Lal, S.; McNally, J.; White, A. J. P.; Díez-González, S. Novel phosphinite and phosphonite copper(I) complexes: Efficient catalysts for click azide-alkyne cycloaddition reactions Organometallics 2011, 30, 6225-6232
22. Miao, T.; Wang, L. Regioselective synthesis of 1,2,3-triazoles by use of a silica-supported copper(I) catalyst Synthesis 2008, 363-368
23. Chassaing, S.; Sido, A. S. S.; Alix, A.; Kumarraja, M.; Pale, P.; Sommer, J. Click chemistry" in zeolites: Copper(I) zeolites as new heterogeneous and ligand-free catalysts for the Huisgen [3 + 2] cycloaddition Chem.-Eur. J. 2008, 14, 6713-6721
24. Lipshutz, B. H.; Taft, B. R. Heterogeneous copper-in-charcoal-catalyzed click chemistry Angew. Chem. 2006, 118, 8415-8418
25. Yamaguchi, K.; Oishi, T.; Katayama, T.; Mizuno, N. A supported copper hydroxide on titanium oxide as an efficient reusable heterogeneous catalyst for 1,3-dipolar cycloaddition of organic azides to terminal alkynes Chem.-Eur. J. 2009, 15, 10464-10472
26. Meng, X.; Xu, X.; Gao, T.; Chen, B. Zn/C-catalyzed cycloaddition of azides and aryl alkynes Eur. J. Org. Chem. 2010, 5409-5414
27. 3 catalyzed selective formation of 1,4-disubstituted triazoles from cycloaddition of alkynes and organic azides J. Org. Chem. 2012, 77, 5844-5849
28. Corma, A.; Garcia, H. Supported gold nanoparticles as catalysts for organic reactions Chem. Soc. Rev. 2008, 37, 2096-2126
29. Mendez, V.; Caps, V.; Daniele, S. Design of hybrid titania nanocrystallites as supports for gold catalysts Chem. Commun. 2009, 3116-3118
30. 2 catalysts prepared by the combination of incipient wetness impregnation and deposition-precipitation J. Catal. 2013, 297, 155-164
31. 2: Structure sensitivity and mechanism J. Catal. 2004, 223, 328-339
32. Rudolph, M.; Hashmi, A. S. K. Gold catalysis in total synthesis-an update Chem. Soc. Rev. 2012, 41, 2448-2462
33. Brouwer, Z.; Li, C.; He, C. Gold-catalyzed organic transformations Chem. Rev. 2008, 108, 3239-3265
34. Corma, A.; Perez, A. L.; Sabater, M. J. Gold-catalyzed carbon-heteroatom bond-forming reactions Chem. Rev. 2011, 111, 1657-1712
35. Hashmi, A. S. K. Homogeneous gold catalysis beyond assumptions and proposals-characterized intermediates Angew. Chem., Int. Ed. 2010, 49, 5232-5241
36. Diebolt, O.; Muller, C.; Vogt, D. On-water" rhodium-catalysed hydroformylation for the production of linear alcohols Catal. Sci. Technol. 2012, 2, 773-777
37. Lindstrom, U. M. Stereoselective organic reactions in water Chem. Rev. 2002, 102, 2751-2772
38. Li, P.; Wang, L. One-pot synthesis of 1,2,3-triazoles from benzyl and alkyl halides, sodium azide and alkynes in water under transition-metal-catalyst free reaction conditions Letters in Organic Chemistry 2007, 4, 23-26
39. Boominathan, M.; Nagaraj, M.; Muthusubramanian, S.; Krishnakumar, R. V. Efficient atom economical one-pot multicomponent synthesis of densely functionalized 4 H -chromene derivatives Tetrahedron 2011, 67, 6057-6064
40. Chitra, S.; Paul, N.; Muthusubramanian, S.; Manisankar, P. A facile, water mediated, microwave-assisted synthesis of 4,6-diaryl-2,3,3a,4-tetrahydro-1 H -pyrido[3,2,1- jk ]carbazoles by a domino Fischer indole reaction- intramolecular cyclization sequence Green Chem. 2011, 13, 2777-2785
41. Paul, N.; Kaladevi, S.; Muthusubramanian, S. Microwave-assisted stereoselective 1,3-dipolar cycloaddition of C, N -diarylnitrone (i.e., N -(arylmethylidene)benzenamine N -oxide) and bis(arylmethylidene)acetone (=1,5-diarylpenta-1,4-dien-3-one): NMR and crystal analysis of diastereoisomeric bis(isoxazolidines) Helv. Chim. Acta 2012, 95, 173-184
42. 2 submicrospheres and their photocatalytic activity Adv. Powder Technol. 2010, 21, 292-297
43. 2 prepared by deposition-precipitation with NaOH and urea J. Catal. 2004, 222, 357-367
44. 3 ligands designed by a fragment-based approach Org. Biomol. Chem. 2010, 8, 1154-1159
45. Santos, A.; El-KaIm, L.; Grimaud, L.; Ronsseray, C. Unconventional oxazole formation from isocyanides Chem. Commun. 2009, 0, 3907-3909
46. 3 nanoflowers via solvent extraction route J. Mater. Sci. Eng. B 2009, 163, 134-137
47. Kidwai, M.; Bansal, V.; Kumar, A.; Mozumdar, S. The first Au-nanoparticles catalyzed green synthesis of propargylamines via a three-component coupling reaction of aldehyde, alkyne and amine Green Chem. 2007, 9, 742-745
48. Asao, N.; Nogami, T.; Lee, S.; Yamamoto, Y. Lewis acid-catalyzed benzannulation via unprecedented [4 + 2] cycloaddition of o -alkynyl(oxo) benzenes and enynals with alkynes J. Am. Chem. Soc. 2003, 125, 10921-10925
49. 3-catalyzed benzannulation: Synthesis of naphthyl ketone derivatives from o-alkynylbenzaldehydes with alkynes J. Am. Chem. Soc. 2002, 124, 12650-12651
50. Borah, B. J.; Dutta, D.; Saikia, P. P.; Barua, N. C.; Dutta, D. K. Stabilization of Cu(0)-nanoparticles into the nanopores of modified montmorillonite: An implication on the catalytic approach for ''click'' reaction between azides and terminal alkynes Green Chem. 2011, 13, 3453-3460
51. 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
52. 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
53. Kantam, M. L.; Jaya, S. V.; Sreedhar, B.; Rao, M. M.; Choudary, B. M. Preparation of alumina supported copper nanoparticles and their application in the synthesis of 1,2,3-triazoles J. Mol. Catal. A: Chem. 2006, 256, 273-277
54. Kaboudin, B.; Abedi, Y.; Yokomatsu, T. One-pot Synthesis of 1,2,3: Triazoles from boronic acids in water using Cu (II)-β-cyclodextrin complex as a nanocatalyst Org. Biomol. Chem. 2012, 10, 4543-4548