Discovery and characterization of catalysts for azide-alkyne cycloaddition by fluorescence quenching

Journal of the American Chemical Society

Volumn 126, Issue 30, 2004, Pages 9152-9153

  Lewis, Warren G ^a   Magallon, Fernando G ^a   Fokin, Valery V ^a   Finn, M G ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; AZIDE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION KINETICS; COMBINATORIAL LIBRARY; CONCENTRATION (PARAMETERS); CYCLOADDITION; FLUORESCENCE; FLUORESCENCE SPECTROSCOPY; ILLUMINATION; REACTION ANALYSIS; SOLUBILITY;

EID: 3343006952     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja048425z     Document Type: Article

References (23)

1. (a) Huisgen, R. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; Vol. 1, pp 1-176.
2. (b) Huisgen, R. Pure Appl. Chem. 1989, 61, 613-628.
3. (a) Mock, W. L.; Irra, T. A.; Wepsiec, J. P.; Manimaran, T. L. J. Org. Chem. 1983, 48, 3619-3620.
4. (b) Mock, W. L.; Irra, T. A.; Wepsiec, J. P.; Adhya, M. J. Org. Chem. 1989, 54, 5302-5308.
5. (c) Lewis, W. G.; Green, L. G.; Grynszpan, F.; Radic, Z.; Carlier, P. R.; Taylor, P.; Finn, M. G.; Sharpless, K. B. Angew., Chem. Int. Ed. 2002, 41, 1053-1057.
6. (d) Wang, Z.-X.; Qin, H.-L. Chem. Commun. 2003, 2450-2451.
7. (a) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2599.
8. (b) Tornøe. C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057-3062.
9. Carruthers, W. In Cycloaddition Reactions in Organic Synthesis; Pergamon Press: New York, 1990; pp 270-331.
10. (a) Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192-3193.
11. (b) Speers, A. E.; Adam, G. C.; Cravatt, B. F. J. Am. Chem. Soc. 2003, 125, 4686-4687.
12. (c) Fazio, F.; Bryan, M. C.; Blixt, O.; Paulson, J. C.; Wong, C.-H. J. Am. Chem. Soc. 2002, 124, 14397-14402.
13. (d) Deiters, A.; Cropp, T. A.; Mukherji, M.; Chin, J. W.; Anderson, J. C.; Schultz, P. G. J. Am. Chem. Soc. 2003, 125, 11782-11783.
14. (e) Link, A. J.; Tirrell, D. A. J. Am. Chem. Soc. 2003, 125, 11164-11165.
15. Zaramella, A.; Conti, N.; Dal Cin, M.; Paio, A.; Seneci, P.; Gehanne, S. J. Comb. Chem. 2001, 3, 410-420.
16. A variety of fluorescence methods have been used for catalysis screening. For example, see: Stambuli, J. P.; Stauffer, S. R.; Shaughnessy, K. H.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 2677-2678; Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 4306-4307. Additional contributions are listed in Supporting Information.
17. A variety of fluorescence methods have been used for catalysis screening. For example, see: Stambuli, J. P.; Stauffer, S. R.; Shaughnessy, K. H.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 2677-2678; Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 4306-4307. Additional contributions are listed in Supporting Information.
18. Berrisford, D. J.; Bolm, C.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1995, 34, 1059-1070.
19. Copper-bipyridine complexes are also well-known catalysts for atom transfer radical polymerization (ATRP) reactions; see Johnson, R. M.; Ng, C.; Samson, C. C. M.; Fraser, C. L. Macromolecules 2000, 33, 8618-8628.
20. Faizullah, A. T.; Townshend, A. Anal. Chim. Acta 1985, 172, 291-296.
21. See Supporting Information for details.
22. If used directly, the values shown in Figure 2 dramatically understate the magnitude of ligand-accelerated catalysis, since the concentration of uncomplexed Cu is much higher than that of Cu-ligand species in all cases.
23. Chan, T. R.; Hilgraf, R.; Sharpless, K. B.; Fokin, V. V. Org. Lett. 2004, in press.