Synthesis of rhodamines from fluoresceins using pd-catalyzed c-n cross-coupling

Organic Letters

Volumn 13, Issue 24, 2011, Pages 6354-6357

  Grimm, Jonathan B ^a   Lavis, Luke D ^a  

^a HOWARD HUGHES MEDICAL INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORESCEIN DERIVATIVE; FLUORESCENT DYE; PALLADIUM; RHODAMINE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; SYNTHESIS;

CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; FLUORESCEINS; FLUORESCENT DYES; MOLECULAR STRUCTURE; PALLADIUM; RHODAMINES;

EID: 84055224080     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol202618t     Document Type: Article

References (35)

1. (a) Haugland, R. P.; Spence, M. T. Z.; Johnson, I. D.; Basey, A. The Handbook: A Guide to Fluorescent Probes and Labeling Technologies, 10th ed.; Molecular Probes: Eugene, OR, 2005.
2. (b) Lavis, L. D.; Raines, R. T. ACS Chem. Biol. 2008, 3, 142.
3. (c) Beija, M.; Afonso, C. A. M.; Martinho, J. M. G. Chem. Soc. Rev. 2009, 38, 2410.
4. (a) Ioffe, I. S.; Zal0manovich, M. Z. Zh. Obshch. Khim. 1962, 32, 1480.
5. (b) Haugland, R. P.; Singer, V. L.; Yue, S. L. U.S. Patent 6,399,392 B1, June 4, 2002.
6. (a) Hug, H.; Los, M.; Hirt, W.; Debatin, K.-M. Biochemistry 1999, 38, 13906.
7. (b) Lavis, L. D.; Chao, T.-Y.; Raines, R. T. ACS Chem. Biol. 2006, 1, 252.
8. (a) Mitchison, T. J.; Sawin, K. E.; Theriot, J. A.; Gee, K.; Mallavarapu, A. Methods Enzymol. 1998, 291, 63.
9. (b) Puliti, D.; Warther, D.; Orange, C.; Specht, A.; Goeldner, M. Bioorg. Med. Chem. 2011, 19, 1023.
10. (c) Wysocki, L. W.; Grimm, J. B.; Tkachuk, A. N.; Brown, T. A.; Betzig, E.; Lavis, L. D. Angew. Chem., Int. Ed. 2011, 50, 11206.
11. High-temperature nucleophilic substitution of dihalofluorans with amines has been used previously but is limited in scope. See ref 2 and: Song, X.; Johnson, A.; Foley, J. J. Am. Chem. Soc. 2008, 130, 17652.
12. Reviews: (a) Hartwig, J. F. In Modern Arene Chemistry; Astruc, D., Ed.; Wiley-VCH: Weinheim, 2002; p 107.
13. (b) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131.
14. (c) Jiang, L.; Buchwald, S. L. In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004; p 699.
15. Woodroofe, C. C.; Lim, M. H.; Bu, W.; Lippard, S. J. Tetrahedron 2005, 61, 3097.
16. Peng, T.; Yang, D. Org. Lett. 2010, 12, 496.
17. (a) Coons, A. H.; Kaplan, M. H. J. Exp. Med. 1950, 91, 1.
18. (b) Sun, W.-C.; Gee, K. R.; Klaubert, D. H.; Haugland, R. P. J. Org. Chem. 1997, 62, 6469.
19. (c) Rossi, F. M.; Kao, J. P. Bioconjugate Chem. 1997, 8, 495.
20. Å hman, J.; Buchwald, S. L. Tetrahedron Lett. 1997, 38, 6363.
21. (a) Huang, X.; Anderson, K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 6653.
22. (b) Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 6338.
23. (a) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251.
24. (b) Chen, A.; Gee, K.; Kang, H.-C. U.S. Patent Appl. US 2010/0291547 A1, Nov. 18, 2010.
25. Old, D. W.; Harris, M. C.; Buchwald, S. L. Org. Lett. 2000, 2, 1403.
26. Bhagwanth, S.; Waterson, A. G.; Adjabeng, G. M.; Hornberger, K. R. J. Org. Chem. 2009, 74, 4634 and references cited therein.
27. Yin, J.; Buchwald, S. L. Org. Lett. 2000, 2, 1101.
28. Hicks, J. D.; Hyde, A. M.; Cuezva, A. M.; Buchwald, S. L. J. Am. Chem. Soc. 2009, 131, 16720.
29. (a) Jones, K. L.; Porzelle, A.; Hall, A.; Woodrow, M. D.; Tomkinson, N. C. O. Org. Lett. 2008, 10, 797.
30. (b) Porzelle, A.; Woodrow, M. D.; Tomkinson, N. C. O. Org. Lett. 2009, 11, 233.
31. Shibata, A.; Furukawa, K.; Abe, H.; Tsuneda, S.; Ito, Y. Bioorg. Med. Chem. Lett. 2008, 18, 2246.
32. Mitronova, G. Y.; Belov, V. N.; Bossi, M. L.; Wurm, C. A.; Meyer, L.; Medda, R.; Moneron, G.; Bretschneider, S.; Eggeling, C.; Jakobs, S.; Hell, S. W. Chem.;Eur. J. 2010, 16, 4477.
33. (a) Lee, L. G.; Berry, G. M.; Chen, C.-H. Cytometry 1989, 10, 151.
34. (b) Furukawa, K.; Abe, H.; Wang, J.; Uda, M.; Koshino, H.; Tsuneda, S.; Ito, Y. Org. Biomol. Chem. 2009, 7, 671.
35. Jin, X.; Uttamapinant, C.; Ting, A. Y. ChemBioChem 2011, 12, 65.