Copper on chitosan: An efficient and easily recoverable heterogeneous catalyst for one pot synthesis of 1,2,3-triazoles from aryl boronic acids in water at room temperature

Tetrahedron Letters

Volumn 56, Issue 15, 2015, Pages 1968-1972

  Anil Kumar, B S P ^a   Harsha Vardhan Reddy, K ^a   Karnakar, K ^a   Satish, G ^a   Nageswar, Y V D ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

1,2,3 Triazoles; Boronic acids; Click reaction; Copper on chitosan (CS); Recyclability

Indexed keywords

1,2,3 TRIAZOLE DERIVATIVE; ACETYLENE; ALKYNE; AZIDE; BORONIC ACID DERIVATIVE; CHITOSAN; COPPER; COPPER COMPLEX; COPPER SULFATE; SODIUM AZIDE; WATER;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CATALYST; CYCLOADDITION; ONE POT SYNTHESIS; ORGANIC CHEMISTRY; REACTION ANALYSIS; ROOM TEMPERATURE; SCANNING ELECTRON MICROSCOPY;

EID: 84925450552     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2015.02.107     Document Type: Article

References (50)

1. H.C. Kolb, M.G. Finn, and K.B. Sharpless Angew. Chem. 113 2001 2056
2. M. Whiting, J. Muldoon, Y.-C. Lin, S.M. Silverman, W. Lindstrom, A.J. Olson, H.C. Kolb, M.G. Finn, K.B. Sharpless, J.H. Elder, and V.V. Fokin Angew. Chem., Int. Ed. 45 2006 1435
3. M.J. Giffin, H. Heaslet, A. Brik, Y.C. Lin, G. Cauvi, C.-H. Wong, D.E. McRee, J.H. Elder, C.D. Stout, and B.E. Torbett J. Med. Chem. 51 2008 6263
4. F. PKrez-Balderas, M. Ortega-MuLoz, J. Morales-Sanfrutos, F. HernMndez-Mateo, F.G. Calvo-Flores, J.A. Calvo-AsNn, J. IsacGarcNa, and F. Santoyo-GonzMlez Org. Lett. 5 2003 1951
5. V.O. Rodionov, S.I. Presolsky, S. Gardinier, Y.-H. Lim, and M.G. Finn J. Am. Chem. Soc. 129 2007 12696
6. S.S. Gupta, J. Kuzelka, P. Singh, W.G. Lewis, M. Manchester, and M.G. Finn Bioconjugate Chem. 16 2005 1572
7. T.R. Chan, R. Hilgraf, K.B. Sharpless, and V.V. Fokin Org. Lett. 6 2004 2853
8. B. Gerard, J. Ryan, A.B. Beeler, and J.A. Porco Jr. Tetrahedron 62 2006 6405
9. V. Aucagne, and D.A. Leigh Org. Lett. 8 2006 4505
10. P. Siemsen, R.C. Livingston, and F. Diederich Angew. Chem., Int. Ed. 39 2000 2632
11. M. Meldal, and W. Tornoe Chem. Rev. 108 2008 2952
12. R. Huisgen, G. Szeimies, and L. Moebius Chem. Ber. 98 1965 4014
13. R. Huisgen Pure Appl. Chem. 61 1989 613
14. R. Huisgen Angew. Chem., Int. Ed. Engl. 2 1963 565
15. E.D. Pressly, R.J. Amir, and C.J. Hawker J. Polym. Sci., Part A: Polym. Chem. 49 2011 814
16. P. Cintas, A. Barge, S. Tagliapietra, L. Boffa, and G. Cravotto Nat. Protoc. 5 2010 607
17. A. Sarkar, T. Mukherjee, and S. Kapoor J. Phys. Chem. C 112 2008 3334
18. D. Raut, K. Wankhede, V. Vaidya, S. Bhilare, N. Darwatkar, A. Deorukhkar, G. Trivedi, and M. Salunkhe Catal. Commun. 10 2009 1240
19. G. Molteni, C.L. Bianchi, G. Marinoni, N. Santo, and A. Ponti New J. Chem. 30 2006 1137
20. L.D. Pachón, J.H. van Maarseveen, and G. Rothenberg Adv. Synth. Catal. 347 2005 811
21. T. Katayama, K. Kamata, K. Yamaguchi, and N. Mizuno ChemSusChem 2 2009 59
22. C. Girard, E. Nen, M. Aufort, S. Beauvire, A. Samson, and J. Herscovici Org. Lett. 8 2006 1689
23. A. Alix, S. Chassaing, P. Pale, and J. Sommer Tetrahedron 64 2008 8922
24. S. Chassaing, A. Sani Souna Sido, A. Alix, M. Kumarraja, P. Pale, and J. Sommer Chem. Eur. J. 14 2008 6713
25. B.H. Lipshutz, and B.R. Taft Angew. Chem. 118 2006 8415 Angew. Chem., Int. Ed. 2006, 45, 8235
26. J.J.E. Hardy, S. Hubert, D.J. Macquarrie, and A.J. Wilson Green Chem. 8 2006 853
27. Chao. Shen, Xu. Jun, Yu. Wenbo, and Pengfei Zhang Green Chem. 16 2014 3007
28. B.C.E. Makhubela, A. Jardine, and G.S. Smith Green Chem. 14 2012 338
29. A.E. Kadib, K. Molvinger, M. Bousmina, and D. Brunel Org. Lett. 12 2010 948
30. B.F. Peirano, V. Thierry, F. Quignard, M. Rabitzer, and E. Guibal J. Membr. Sci. 329 2009 30
31. D.J. Macquarrie, and J.J.E. Hardy Ind. Eng. Chem. Res. 44 2005 8499
32. E. Guibal, V. Thierry, and B.F. Peirano Ion Exch. Solvent Extr. 18 2007 151
33. S.-S. Yi, D.-H. Lee, E. Sin, and Y.-S. Lee Tetrahedron Lett. 48 2007 6771
34. S.E.S. Leonhardt, A. Stolle, B. Ondruschka, G. Cravotto, C. De Leo, K.D. Jandt, and T.F. Keller Appl. Catal. A 379 2010 30
35. B.S.P.A. Kumar, B. Madhav, K.H.V. Reddy, and Y.V.D. Nageswar Tetrahedron Lett. 52 2011 2862
36. B.S.P. Anil-Kumar, K. Harsha Vardhan Reddy, B. Madhav, K. Ramesh, and Y.V.D. Nageswar Tetrahedron Lett. 53 2012 4595
37. K.H.V. Reddy, V.P. Reddy, J. Shankar, B. Madhav, B.S.P.A. Kumar, and Y.V.D. Nageswar Tetrahedron Lett. 52 2011 2679
38. K.H.V. Reddy, V.P. Reddy, J. Shankar, and Y.V.D. Nageswar Synlett 2011 1268
39. K.H.V. Reddy, A.A. Kumar, G. Kranthi, and Y.V.D. Nageswar Beilstein J. Org. Chem. 7 2011 886
40. G. Satish, K.H.V. Reddy, K. Ramesh, and K. Karnakar Tetrahedron Lett. 53 2012 2518
41. K.H.V. Reddy, G. Satish, K. Ramesh, K. Karnakar, and Y.V.D. Nageswar Chem. Lett. 41 2012 585
42. B. Madhav, S. Narayana Murthy, B.S.P. Anil Kumar, K. Ramesh, and Y.V.D. Nageswar Tetrahedron Lett. 53 2012 3835
43. K. Ramesh, K. Karnakar, G. Satish, B.S.P. Anil Kumar, and Y.V.D. Nageswar Tetrahedron Lett. 53 2012 6936
44. K. Harsha Vardhan Reddy, G. Satish, V. Prakash Reddy, B.S.P. Anil Kumar, and Y.V.D. Nageswar RSC Adv. 2 2012 11084
45. G. Satish, K.H.V. Reddy, K. Ramesh, B.S.P. Anil Kumar, and Y.V.D. Nageswar Tetrahedron Lett. 55 2014 2596
46. K.H.V. Reddy, G. Satish, K. Ramesh, K. Karnakar, and Y.V.D. Nageswar Tetrahedron Lett. 53 2012 3061
47. G. Satish, K.H.V. Reddy, B.S.P. Anil kumar, J. Shankar, R. Uday kumar, and Y.V.D. Nageswar Tetrahedron Lett. 55 2014 5533
48. K. Harsha Vardhan Reddy, B.S.P. Anil Kumar, V. Prakash Reddy, R. Uday kumar, and Y.V.D. Nageswar RSC Adv. 4 2014 45579
49. K. Swapna, S.N. Murthy, M.T. Jyothi, and Y.V.D. Nageswar Org. Biol. Chem. 9 2011 5989
50. R.B. Nasir Baig, and R.S. Varma Green Chem. 15 2013 1839