Novel rhodamine dyes via suzuki coupling of xanthone triflates with arylboroxins

Synlett

Volumn , Issue 1, 2010, Pages 89-92

  Calitree, Brandon D ^a   Detty, Michael R ^a  

^a UNIVERSITY AT BUFFALO   (United States)

Author keywords

Arylations; Arylboroxins; Palladium; Rhodamine dyes; Suzuki coupling

Indexed keywords

ARYLBOROXIN; BENZENEBORONIC ACID; BORON DERIVATIVE; PALLADIUM; RHODAMINE; SELENOXANTHONE; TELLUROXANTHONE; THIOXANTHENE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG; XANTHONE DERIVATIVE;

ARTICLE; ARYLATION; DRUG SYNTHESIS; ISOMER; QUANTUM YIELD; SUZUKI REACTION;

EID: 77951692301     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1218535     Document Type: Article

References (46)

1. As laser dyes, fluorescent labels, and probes: (a) Peterson, O. G.; Tuccio, S. A.; Snavely, B. B. Appl. Phys. Lett. 1970, 17, 245.
2. (b) Drexhage, K. H. Top. Appl. Phys. 1973, 1, 144.
3. (c) Karstens, T.; Kobs, K. J. Phys. Chem. 1980, 84, 1871.
4. (d) Preminger, C.; Mohr, G. J.; Klimant, I.; Wolfbeis, O. S. Anal. Chim. Acta 1996, 334, 113.
5. (e) Liu, J.; Diwu, Z.; Leung, W.-Y.; Lu, Y.; Patch, B.; Hugland, R. P. Tetrahedron Lett. 2003, 44, 4355.
6. (f) Beija, M.; Afonso, C. A. M.; Martinho, J. M. G. Chem. Soc. Rev. 2009, 38, 2410.
7. Biosensing with FRET: (a) Adams, S. R.; Harootounian, A. T.; Buechler, Y. J.; Taylos, S. S.; Tsien, R. Y. Nature (London) 1991, 349, 694.
8. (b) Martinez-Manez, R.; Sancenon, F. Chem. Rev. 2003, 103, 4419.
9. Electrochemiluminescence: Richter, M. M. Chem. Rev. 2004, 104, 3003.
10. Proton sensors: (a) de Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515.
11. (b) Vogel, M.; Rettig, W.; Sens, D.; Drexhage, K. H. Chem. Phys. Lett. 1988, 147, 452.
12. Halide sensors: Anzenbacher, P. Jr.; Jursikova, K.; Sessler, J. L. J. Am. Chem. Soc. 2000, 122, 9350.
13. (a) Johnson, L. V.; Walsh, M. L.; Bockus, B. J.; Chen, L. B. J. Cell. Biol. 1981, 88, 526.
14. (b) Davis, S.; Weiss, M. J.; Wong, J. R.; Lampidis, T. J.; Chen, L. B. J. Biol. Chem. 1985, 260, 13844.
15. (c) Bernai, S. D.; Lampdis, T. J.; Mclsaac, R. M.; Chen, L. B. Science 1986, 222, 169.
16. (a) Tombline, G.; Donnelly, D. J.; Holt, J. J.; You, Y.; Ye, M.; Gannon, M. K.; Nygren, C. L.; Detty, M. R. Biochemistry 2006, 45, 8034.
17. (b) Tombline, G.; Holt, J. J.; Gannon, M. K. II.; Donnelly, D. J.; Wetzel, B.; Sawada, G. A.; Raub, T. J.; Detty, M. R. Biochemistry 2008, 47, 3294.
18. (c) Gannon, M. K. II.; Holt, J. J.; Bennett, S. M.; Wetzel, B. R.; Loo, T. W.; Bartlett, M. C.; Clarke, D. M.; Sawada, G. A.; Higgins, J. W.; Tombline, G.; Raub, T. J.; Detty, M. R. J. Med. Chem. 2009, 52, 3328.
19. (a) Brasseur, N.; Menard, I.; Forget, A.; El Jastimi, R.; Hamel, R.; Molfino, N. A.; van Lier, J. E. Photochem. Photobiol. 2000, 72, 780.
20. (b) Pal, P.; Zeng, H.; Durocher, G.; Girard, D.; Li, T. C.; Gupta, A. K.; Giasson, R.; Blanchard, L.; Gaboury, L.; Balassy, A.; Turmel, C.; Laperriere, A.; Villeneuve, L. Photochem. Photobiol. 1996, 53, 161.
21. (a) Shi, J.; Zhang, X.; Neckers, D. C. J. Org. Chem. 1992, 57, 4418.
22. (b) Parker, C. A. In Advances in Photochemistry, Vol.2; Noyes, W. A. Jr.; Hammond, G. S.; Pitts, J. N. Jr., Eds.; Wiley Interscience: New York, 1964, 305.
23. (a) Ohulchanskyy, T.; Donnelly, D. J.; Detty, M. R.; Prasad, P. N. J. Phys. Chem. B 2004, 108, 8668.
24. (b) Wagner, S. J.; Skripchenko, A.; Donnelly, D. J.; Ramaswamy, K.; Detty, M. R. Bioorg. Med. Chem, 2005, 13, 5927.
25. (c) Gibson, S. L.; Holt, J. J.; Ye, M.; Donnelly, D. J.; Ohulchanskyy, T. Y.; You, Y.; Detty, M. R. Bioorg. Med. Chem. 2005, 13, 6394.
26. (d) Wagner, S. J.; Skripchenko, A.; ThompsonMontgomery, D.; Awatefe, H.; Donnelly, D. J.; Detty, M. R. Photochem. Photobiol. 2006, 76, 514.
27. Detty, M. R.; Gibson, S. L.; Wagner, S. J. Med. Chem. 2004, 47, 3897.
28. (a) Woodroofe, C. C.; Lim, M. H.; Bu, W.; Lippard, S. J. Tetrahedron 2005, 61, 3097.
29. (b) Ioffe, I. S.; Otten, V. F. Zh. Obsh. Khim. 1962, 32, 1477.
30. (a) Bandichhor, R.; Petrescu, A. D.; Vespa, A.; Kier, A. B.; Schroeder, F.; Burgess, K. Bioconjugate Chem. 2006, 17, 1219.
31. (b) Jiao, G.-S.; Castro, J. C.; Thoresen, L. H.; Burgess, K. Org. Lett. 2005, 5, 3675.
32. (a) Gannon, M. K. II; Detty, M. R. J. Org. Chem. 2007, 72, 2647.
33. (b) Calitree, B. D.; Donnelly, D. J.; Holt, J. J.; Gannon, M. K. II; Nygren, C.; Sukumaran, D. K.; Autschbach, J.; Detty, M. R. Organometallics 2007, 26, 6248.
34. Wu, L.; Burgess, K. Org. Lett. 2009, 10, 1779.
35. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
36. (a) Washburn, R. M.; Levens El Albright, C. F.; Billig, F. A. Org. Synth, Coll. Vol.4 1963, 68.
37. (b) Wu, X.; Liu, X.; Zhao, G. Tetrahedron: Asymmetry 2005, 16, 2299.
38. Tsukamoto, H.; Uchiyama, T.; Suzuki, T.; Kondo, Y. Org. Biomol. Chem. 2008, 6, 3005.
39. Cioffi, C. L.; Spencer, W. T.; Justin, J.; Richards, J. J.; Herr, R. J. J. Org. Chem. 2004, 69, 2210.
40. 2O, and the dye was collected by filtration. The ion exchange was repeated for a total of 3 times. The success of the ion exchange was confirmed by elemental analysis (±0.4% in C, H, N).
41. 3+: 387.1703; found: 387.1720.
42. 2S+: 403.1475; found: 403.1468.
43. 3+: 387.1703; found: 387.1704.
44. 2S+: 403.1475; found: 403.1467.
45. 3+: 388.1656; found: 388.1660.
46. 2S+: 404.1427; found: 404.1420.