One-pot procedure for diazo transfer and azide-alkyne cycloaddition: Triazole linkages from amines

Organic Letters

Volumn 9, Issue 1, 2007, Pages 1-4

  Beckmann, Henning S G ^a   Wittmann, Valentin ^a  

^a UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; AMINE; AZIDE; AZO COMPOUND; TRIAZOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; GLYCOSYLATION;

ALKYNES; AMINES; AZIDES; AZO COMPOUNDS; GLYCOSYLATION; MOLECULAR STRUCTURE; TRIAZOLES;

EID: 33846416915     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0621506     Document Type: Article

References (46)

1. (a) Huisgen, R. Angew. Chem., Int. Ed. Engl. 1963, 2, 565-598.
2. (b) Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057-3064.
3. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2599.
4. (a) Lee, L. V.; Mitehell, M. L.; Huang, S.-J.; Fokin, V. V.; Sharpless, K. B.; Wong, C.-H. J. Am. Chem. Soc. 2003, 125, 9588-9589.
5. (b) Brik, A.; Muldoon, J.; Lin, Y.-C.; Elder, J. H.; Goodsell, D. S.; Olson, A. J.; Fokin, V. V.; Sharpless, K. B.; Wong, C.-H. ChemBioChem 2003, 4, 1246-1248.
6. (a) Wu, P.; Feldman, A. K.; Nugent, A. K.; Hawker, C. J.; Scheel, A.; Voit, B.; Pyun, J.; Fréchet, J. M. J.; Sharpless, K. B.; Fokin, V. V. Angew. Chem., Int. Ed. 2004, 43, 3928-3932.
7. (b) Helms, B.; Mynar, J. L.; Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 2004, 126, 15020-15021.
8. (c) van Steenis, D. J. V. C.; David, O. R. P.; van Strijdonck, G. P. F.; van Maarseveen, J. H.; Reek, J. N. H. Chem. Commun. 2005, 4333-4335.
9. Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192-3193.
10. (a) Speers, A. E.; Adam, G. C.; Cravatt, B. F. J. Am. Chem. Soc. 2003, 125, 4686-4687.
11. (b) Link, A. J.; Tirell, D. A. J. Am. Chem. Soc. 2003, 125, 11164-11165.
12. (c) Burley, G. A.; Gierlich, J.; Mofid, M. R.; Nir, H.; Tal, S.; Eichen, Y.; Carell, T. J. Am. Chem. Soc. 2006, 128, 1398-1399.
13. (a) Mammen, M.; Choi, S.-K.; Whitesides, G. M. Angew. Chem., Int. Ed. 1998, 37, 2754-2794.
14. (b) Kiessling, L. L.; Gestwicki, J. E.; Strong, L. E. Angew. Chem., Int. Ed. 2006, 45, 2348-2368.
15. (a) Pérez-Balderas, F.; Ortega-Munoz, M.; Morales-Sanfrutos, J.; Hernández-Mateo, F.; Calvo-Flores, F. G.; Calvo-Asín, J. A.; Isac-Gacía, J.; Santojo-González, F. Org. Lett. 2003, 5, 1951-1954.
16. (b) Tejler, J.; Tullberg, E.; Frejd, T.; Leffler, H.; Nilsson, U. J. Carbohydr. Res. 2006, 341, 1353-1362.
17. Joosten, J. A. F.; Tholen, N. T. H.; Maate, F. A. E.; Brouwer, A. J.; van Esse, G. W.; Rijkers, D. T. S.; Liskamp, R. M. J.; Pieters, R. J. Eur. J. Org. Chem 2005, 3182-3185.
18. Chittaboina, S.; Fang, X.; Wang, Q. Tetrahedron Lett. 2005, 46, 2331-2336.
19. Bräse, S.; Gil, C.; Knepper, K.; Zimmermann, V. Angew. Chem., Int. Ed. 2005, 44, 5188-5240.
20. (a) Feldman, A. K.; Colasson, B.; Fokin, V. V. Org. Lett. 2004, 6, 3897-3899.
21. (b) Appukkuttan, P.; Dehaen, W.; Fokin, V. V.; Van der Eycken, E. Org. Lett. 2004, 6, 4223-4225.
22. (a) Cavender, C. J.; Shiner, V. J. J. Org. Chem. 1972, 37, 3567-3569.
23. (b) Vasella, A.; Witzig, C.; Chiara, J.-L.; Martin-Lomas, M. Helv. Chim. Acta 1991, 74, 2073-2077.
24. (c) Alper, P. B.; Hung, S.-C.; Wong, C.-H. Tetrahedon Lett. 1996, 37, 6029-6032.
25. Nyffeler, P. T.; Liang, C.-H.; Koeller, K. M.; Wong, C.-H. J. Am. Chem. Soc. 2002, 124, 10773-10778.
26. Lundquist, J. T.; Pelletier, J. C. Org. Lett. 2001, 3, 781-783.
27. Himo, F.; Lovell, T.; Hilgraf, R.; Rostovtsev, V. V.; Noodleman, L.; Sharpless, K. B.; Fokin, V. V. J. Am. Chem. Soc. 2005, 127, 210-216.
28. (a) Chan, T. R.; Hilgraf, R.; Sharpless, K. B.; Fokin, V. V. Org. Lett. 2004, 6, 2853-2855.
29. (b) Lewis, W. G.; Magallon, F. G.; Fokin, V. V.; Finn, M. G. J. Am. Chem. Soc. 2004, 126, 9152-9153.
30. (a) Gabius, H.-J.; Siebert, H.-C.; André, S.; Jiménez- Barbero, J.; Rüdiger, H. ChemBioChem 2004, 5, 740-764.
31. (b) Dam, T. K.; Brewer, C. F. Chem. Rev. 2002, 102, 387-429.
32. (a) Wittmann, V. In Highlights in Bioorganic Chemistry: Methods and Applications; Schmuck, C., Wennemers, H., Eds.; Wiley-VCH: Weinheim, 2004; pp 203-213.
33. (b) Wittmann, V.; Seeberger, S. Angew. Chem., Int. Ed. 2004, 43, 900-903.
34. (c) Wittmann, V.; Seeberger, S. Angew. Chem., Int. Ed. 2000, 39, 4348-4352.
35. (d) Choi, S.-K. Synthetic Multivalent Molecules. Concepts and Biomedical Applications; John Wiley & Sons: Hoboken, NJ, 2004.
36. (e) Lundquist, J. J.; Toone, E. J. Chem. Rev. 2002, 102, 555-578.
37. (f) Lindhorst, T. K. Top. Curr. Chem. 2002, 218, 201-235.
38. (g) Roy, R.; Baek, M.-G. Rev. Mol. Biotechnol. 2002, 90, 291-309.
39. (a) Cho, S. H.; Yoo, E. J.; Bae, I.; Chang, S. J. Am. Chem. Soc. 2005, 127, 16046-16057.
40. (b) Cassidy, M. P.; Raushel, J.; Fokin, V. V. Angew. Chem., Int. Ed. 2006, 45, 3154-3157.
41. (c) Whiting, M.; Fokin, V. V. Angew. Chem., Int. Ed. 2006, 45, 3157-3161.
42. (a) Hassner, A.; Stern, M. Angew. Chem., Int. Ed. 1986, 25, 478-479.
43. (b) Hassner, A.; Stern, M.; Gottlieb, H. E. J. Org. Chem. 1990, 55, 2304-2306.
44. (c) Dharanipragada, R.; VanHulle, K.; Bannister, A.; Bear. S.; Kennedy, L.; Hruby, V. J. Tetrahedron 1992, 48, 4733-4748.
45. Titz, A.; Radic, Z.; Schwardt, O.; Ernst, B. Tetrahedron Lett. 2006, 47, 2383-2385.
46. It has to be noted that even if diazidomethane is formed, it would be converted to stable triazole derivatives in the subsequent azide-alkyne cycloadditions. However, we could never identify side products resulting from such a reaction.