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Silica Functionalized Cu(I) as a Green and Recyclable Heterogeneous Catalyst for the Huisgen 1,3-Dipolar Cycloaddition in Water at Room Temperature

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Abstract

Silica functionalized Cu(I) is reported as a green and recyclable heterogeneous catalyst for the regioselective synthesis of 1,4-disubstituted-1,2,3-triazoles via Huisgen 1,3-dipolar cycloaddition reaction between terminal alkynes, benzyl/allyl/alkyl halides and NaN3 in water at room temperature. The azide intermediate do not need to be isolated, which make this procedure highly economical. Further, silica functionalized Cu(I) could be recovered by simple filtration and recycled up to 7 consecutive runs without loss of significant activity. The catalyst is characterized by FTIR, thermal analysis, SEM, TEM and AAS.

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References

  1. Thomas JM, Thomas WJ (1997) In principles and practice of heterogeneous catalysis. VCH, Weinheim

    Google Scholar 

  2. Blaser HU, Baiker A, Prins R (1997) In heterogeneous catalysis and fine chemicals IV. Elsevier, Netherlands

    Google Scholar 

  3. Reddy BM, Reddy GK, Rao KN, Khan A, Ganesh I (2007) J Mol Catal A Chem 265:276

    Article  CAS  Google Scholar 

  4. Cho YS, Park JC, Lee B, Kim Y, Yi J (2002) Catal Lett 81:89

    Article  CAS  Google Scholar 

  5. Fey T, Fischer H, Bachmann S, Albert K, Bolm C (2001) J Org Chem 66:8154

    Article  CAS  Google Scholar 

  6. Polshettiwar V, Len C, Fihri A (2009) Co-ord Chem Rev 253:2599

    Article  CAS  Google Scholar 

  7. Paul S, Clark JH (2004) J Mol Catal A Chem 215:107

    Article  CAS  Google Scholar 

  8. Choudhary D, Paul S, Gupta R, Clark JH (2006) Green Chem 9:431

    Google Scholar 

  9. Shamim T, Gupta M, Paul S (2009) J Mol Catal A Chem 302:15

    Article  CAS  Google Scholar 

  10. Shamim T, Choudhary D, Mahajan S, Gupta R, Paul S (2009) Catal Commun 10:1931

    Article  CAS  Google Scholar 

  11. Minakata S, Komatsu M (2009) Chem Rev 109:711

    Article  CAS  Google Scholar 

  12. Gu Y, Karam A, Jerome F, Barrault J (2007) Org Lett 9:3145

    Article  CAS  Google Scholar 

  13. Isobe K, Hoshi T, Suzuki T, Hagiwara H (2005) Mol Divers 9:317

    Article  CAS  Google Scholar 

  14. Gu Y, Ogawa C, Kobayashi J, Mori Y, Kobayashi S (2006) Angew Chem 118:7375

    Article  Google Scholar 

  15. Huisgen R, Szeimies G, Moebius L (1967) Chem Ber 100:2494

    Article  CAS  Google Scholar 

  16. Huisgen R (1984) In: Padwa A (ed) 1, 3-diplar cycloaddition chemistry. Wiley, New York

    Google Scholar 

  17. Huisgen R (1989) Pure Appl Chem 61:613

    Article  CAS  Google Scholar 

  18. Gil MV, Arevalo MJ, Lopez O (2007) Synthesis 1589

  19. Tornoe CW, Christensen C, Meldal M (2002) J Org Chem 67:3057

    Article  CAS  Google Scholar 

  20. Rostovtsev VV, Green LG, Fokin VV, Sharpless KB (2002) Angew Chem Int Ed 41:2596

    Article  CAS  Google Scholar 

  21. Li P, Wang L (2007) Lett Org Chem 4:23

    Article  Google Scholar 

  22. Lutz J-F (2008) Angew Chem Int Ed 47:2182

    Article  CAS  Google Scholar 

  23. Bock VD, Hiemstra H, Van Maarseveen JH (2006) Eur J Org Chem 51

  24. Meldal M, Tornoe CW (2008) Chem Rev 108:2952

    Article  CAS  Google Scholar 

  25. Scriven EFV, Turnbull K (1988) Chem Rev 88:297

    Article  CAS  Google Scholar 

  26. Maksikova AV, Serebryakova ES, Tikhonova LG, Vereshchagin LI (1980) Chem Heterocycl Comp 1284

  27. Miao T, Wang L (2008) Synthesis 363

  28. Li P, Wang L, Zhang Y (2008) Tetrahedron 64:10825

    Article  CAS  Google Scholar 

  29. Sirion U, Bae YJ, Lee BS, Chi DY (2008) Synlett 2326

  30. Girard C, Onen E, Aufort M, Beauviere S, Samson E, Herscovici J (2006) Org Lett 8:1689

    Article  CAS  Google Scholar 

  31. Jlalia I, Elamari H, Meganem F, Herscovici J, Girarad C (2008) Tetrahedron Lett 49:6756

    Article  CAS  Google Scholar 

  32. Alonso F, Moglie Y, Radivoy G, Yus M (2009) Tetrahedron Lett 50:2358

    Article  CAS  Google Scholar 

  33. Raul D, Wankhede K, Vaidya V, Bhilare S, Darwatkar N, Deorukhkar A, Trivedi G, Salunkhe M (2009) Catal Commun 10:1240

    Article  Google Scholar 

  34. Chassaing S, Kumarraja M, Sido ASS, Pale P, Sommer J (2007) Org Lett 9:883

    Article  CAS  Google Scholar 

  35. Lee C-T, Huang S, Lipshutz BH (2009) Adv Synth Catal 351:3139

    Article  CAS  Google Scholar 

  36. Gonda Z, Novak Z (2010) Dalton Trans 39:726

    Article  CAS  Google Scholar 

  37. Mobofu EB, Clark JH, Macquarrie DJ (2001) Green Chem 3:23

    Article  Google Scholar 

  38. Mathew P (2008) J Am Chem Soc 130:13534

    Article  CAS  Google Scholar 

  39. Tsypin GI (1975) Zhur Org Khimii 11:1395

    CAS  Google Scholar 

  40. Kacprzak K (2005) Synlett 943

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Acknowledgement

We are grateful to SAIF, Punjab University, Chandigarh for SEM and TEM; Head, Institute Instrumentation Centre, Indian Institute of Technology, Roorkee for TGA; and SAIF, Nagpur University, Nagpur for AAS analysis.

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Correspondence to Satya Paul.

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Shamim, T., Paul, S. Silica Functionalized Cu(I) as a Green and Recyclable Heterogeneous Catalyst for the Huisgen 1,3-Dipolar Cycloaddition in Water at Room Temperature. Catal Lett 136, 260–265 (2010). https://doi.org/10.1007/s10562-010-0330-3

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