Chemoselective formation of successive triazole linkages in one pot: "Click-click" chemistry

Organic Letters

Volumn 8, Issue 20, 2006, Pages 4505-4507

  Aucagne, Vincent ^a,b   Leigh, David A ^a  

^a UNIVERSITY OF EDINBURGH   (United Kingdom)

^b UNIVERSITÉ D'ORLÉANS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33750086062     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061657d     Document Type: Article

References (26)

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7. For a recent review, see: Bock, V. D.; Hiemstra, H.; van Maarseveen, J. H. Eur. J. Org. Chem. 2006, 51-68.
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10. Aucagne, V.; Hänni, K. D.; Leigh, D. A.; Lusby, P. J.; Walker, D. B. J. Am. Chem. Soc. 2006, 128, 2186-2187.
11. 7
12. 1H NMR, ESI-MS).
13. In many reports, the alkyne moiety is introduced as its TMS derivative, which is deprotected, worked up, and purified prior to clicking. See, for example: (a) Malkoch, M.; Thibault, R. J.; Drockenmuller, E.; Messerschmidt, M.; Voit, B.; Russell, T. P.; Hawker, C. J. J. Am. Chem. Soc. 2005, 127, 14942-14949.
14. (b) Helms, B.; Mynar, J. L.; Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 2005, 127, 15020-15021.
15. (c) Suh, B.-C.; Jeon, H. B.; Posner, G. H.; Silverman, S. M. Tetrahedron Lett. 2004, 45, 4623-4625.
16. Several recent articles illustrate the efficacy of click chemistry for the ligation of peptide building blocks. See, for example: (a) Horne, W. S.; Yadav, M. K.; Stout, C. D.; Ghadiri, M. R. J. Am. Chem. Soc. 2004, 126, 15366-15367.
17. (b) Rijkers, D. T. S.; van Esse, G. W.; Merkx, R.; Brouwer, A. J.; Jacobs, H. J. F.; Pieters, R. J.; Liskamp, R. M. J. Chem. Commun. 2005, 36, 4581-4583.
18. (c) Franke, R.; Doll, C.; Eichler, J. Tetrahedron Lett. 2005, 46, 4479-4482.
19. (d) Dirks, A. J. T.; van Berkel, S. S.; Hatzakis, N. S.; Opsteen, J. A.; van Delft, F. L.; Cornelissen, J. J. L. M.; Rowan, A. E.; van Hest, J. C. M.; Rutjes, F. P. J. T.; Nolte, R. J. M. Chem. Commun. 2005, 33, 4172-4174.
20. (e) Jang, H.; Fafarman, A.; Holub, J. M.; Kirshenbaum, K. Org. Lett. 2005, 7, 1951-1954.
21. (f) Musiol, H.-J.; Dong, S.; Kaiser, M.; Bausinger, R.; Zumbusch, A.; Bertsch, U.; Moroder, L. Chem. Bio. Chem. 2005, 625-628.
22. (g) Holub, J. M.; Jang, H.; Kirshenbaum, K. Org. Biomol. Chem. 2006, 4, 1497-1502.
23. (h) Bock, V. D.; Perciaccante, R.; Jansen, T. P.; Hiemstra, H.; van Maarseveen, J. H. Org. Lett. 2006, 8, 919-922.
24. CAUTION: Low molecular weight azides can be explosive. For a recent review covering various aspects of azide chemistry, see: Bräse, S.; Gil, C.; Knepper, K.; Zimmermann, V. Angew. Chem., Int. Ed. 2005, 44, 5188-5240.
25. Tagged or solid-supported alkynyl "azide-quenching" agents could allow excess reactants to be used in both cycloaddition steps, probably enabling the overall yield to be increased still further.
26. Cu(I)-mediated cleavage of an alkyne C-Si bond has been reported: Ito, H.; Arimoto, K.; Sensui, H-o; Hosomi, A. Tetrahedron Lett. 1997, 38, 3977-3980. We are currently developing more robust terminal alkyne protecting groups.