Hydroxyapatite-supported copper(II)-catalyzed azide-alkyne [3+2] cycloaddition with neither reducing agents nor bases in water

Tetrahedron Letters

Volumn 52, Issue 51, 2011, Pages 6916-6918

  Masuyama, Yoshiro ^a   Yoshikawa, Kazuki ^a   Suzuki, Noriyuki ^a   Hara, Kenji ^b   Fukuoka, Atsushi ^b  

^a SOPHIA UNIVERSITY   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Azide alkyne 3+2 cycloaddition; Copper(II) exchanged hydroxyapatite; Environmentally benign process; Reusable heterogeneous catalyst

Indexed keywords

ALKYNE DERIVATIVE; AZIDE; CUPRIC ION; HYDROXYAPATITE; WATER;

AIR; ARTICLE; CATALYST; CYCLOADDITION;

EID: 81255214589     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.10.060     Document Type: Article

References (26)

1. V.V. Rostovtsev, L.G. Green, V.V. Fokin, and K.B. Sharpless Angew. Chem., Int. Ed. 41 2002 2596
2. C.W. Tornøe, C. Christensen, and M. Meldal J. Org. Chem. 67 2002 3057
3. M. Meldal, and C.W. Tornøe Chem. Rev. 108 2008 2952
4. H.C. Kolb, and K.B. Sharpless Drug Discovery Today 8 2003 1128
5. J.-F. Lutz Angew. Chem., Int. Ed. 46 2007 1018
6. V.D. Bock, H. Hiemstra, and J.H. van Maarseveen Eur. J. Org. Chem. 2006 51
7. F. Himo, T. Lovell, R. Hilgraf, V.V. Rostovtsev, L. Noodleman, K.B. Sharpless, and V.V. Fokin J. Am. Chem. Soc. 127 2005 210
8. J.E. Hein, and V.V. Fokin Chem. Soc. Rev. 39 2010 1302
9. S. Chassaing, A.S.S. Sido, A. Alix, M. Kumarraja, P. Pale, and J. Sommer Chem. Eur. J. 14 2008 6713
10. T. Shamim, and S. Paul Catal. Lett. 136 2010 260
11. C. Girard, E. Önen, M. Aufort, S. Beauvire, E. Samaon, and J. Herscovici Org. Lett. 8 2006 1689
12. H.A. Orgueira, D. Fokas, Y. Isome, P.C.-M. Chan, and C.M. Baldino Tetrahedron Lett. 46 2005 2911
13. I.S. Park, M.S. Kwon, Y. Kim, J.S. Lee, and J. Park Org. Lett. 10 2008 497
14. B.H. Lipshutz, and B.R. Taft Angew. Chem., Int. Ed. 45 2006 8235
15. K. Kamata, Y. Nakagawa, K. Yamaguchi, and N. Mizuno J. Am. Chem. Soc. 130 2008 15304 and references cited therein
16. W.S. Brotherton, H.A. Michaels, J.T. Simmons, R.J. Clark, N.S. Dalal, and L. Zhu Org. Lett. 11 2009 4954
17. G.-C. Kuang, H.A. Michaels, J.T. Simmons, R.J. Clark, and L. Zhu J. Org. Chem. 75 2010 6540
18. G.-C. Kuang, P.M. Guha, W.S. Brotherton, J.T. Simmons, L.A. Stankee, B.T. Nguyen, R.J. Clark, and L. Zhu J. Am. Chem. Soc. 133 2011 13984 and references cited therein
19. K.R. Reddy, K. Rajgopal, and M.L. Kantam Catal. Lett. 114 2007 36
20. K. Namitharan, M. Kumarraja, and K. Pitchumani Chem. Eur. J. 15 2009 2755
21. K. Kaneda, K. Mori, T. Hara, T. Mizugaki, and K. Ebitani Catal. Surv. Asia 8 2004 231
22. K. Mori, T. Hara, T. Mizugaki, K. Ebitani, and K. Kaneda J. Am. Chem. Soc. 126 2004 10657
23. Y. Masuyama, Y. Nakajima, and J. Okabe Appl. Catal. A Gen. 387 2010 107
24. B.M. Choudary, C. Sridhar, M.L. Kantam, and B. Sreedhar Tetrahedron Lett. 45 2004 7319
25. T. Kanazawa Inorganic Phosphate Materials 1989 Kodansha Tokyo Elsevier: Amsterdam, p. 15
26. J.C. Elliott Structure and Chemistry of the Apatites and Other Orthophosphates 1994 Elsevier Amsterdam p. 111