Preparation of amphiphilic glycerol-substituted zinc phthalocyanines using copper-free Sonogashira cross-coupling in aqueous medium

Tetrahedron Letters

Volumn 52, Issue 34, 2011, Pages 4395-4397

  Dumoulin, Fabienne ^a   Ali, Hasrat ^b   Ahsen, Vefa ^a   Van Lier, Johan E ^b  

^a GEBZE TECHNICAL UNIVERSITY   (Turkey)

^b UNIVERSITY OF SHERBROOKE   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; GLYCEROL; MONOIODOTRIGLYCEROL; PALLADIUM; PHTHALOCYANINE ZINC; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; MASS SPECTROMETRY; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SONOGASHIRA REACTION; ULTRAVIOLET SPECTROSCOPY;

EID: 79960835045     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.06.010     Document Type: Article

References (31)

1. M. Victoria Martinez-Diaz, M. Quintiliani, and T. Torres Synlett 2008 1 20
2. H. Ali, and J.E. van Lier K.M. Kadish, K.M. Smith, R. Guilard, Handbook of Porphyrin Science, Phototherapy, Radioimmunotherapy and Imaging, Vol. 4 2010 World Scientific Publishing Co. Pte. Ltd. Hackensack, NJ, USA 1 120
3. F. Dumoulin, M. Durmus, V. Ahsen, and T. Nyokong Coord. Chem. Rev. 254 2010 2792 2847
4. H. Ali, O. St-Jean, J.-P. Tremblay-Morin, and J.E. van Lier Tetrahedron Lett. 47 2006 8275 8278
5. N. Cauchon, H. Tian, R. Langlois, C. La Madeleine, S. Martin, H. Ali, D. Hunting, and J.E. van Lier Bioconjugate Chem. 16 2005 80 89
6. J.E. van Lier, H. Tian, H. Ali, N. Cauchon, and H.M. Hassessian J. Med. Chem. 52 2009 4107 4110
7. H. Tian, H. Ali, and J.E. van Lier Tetrahedron Lett. 41 2000 8435 8438
8. M. di Ramesh Reddy, N. Shibata, H. Yoshiyama, S. Nakamura, and T. Toru Synlett 2007 628 632
9. H. Ali, N. Cauchon, and J.E. van Lier Photochem. Photobiol. Sci. 8 2009 868 874
10. J.-P. Tremblay-Morin, H. Ali, and J.E. van Lier Tetrahedron Lett. 46 2005 6999 7002
11. J.-P. Tremblay-Morin, H. Ali, and J.E. van Lier Tetrahedron Lett. 47 2006 3043 30462
12. H. Ali, and J.E. Van Lier Chem. Rev. 99 1999 2379 2450
13. C.M. Allen, W.M. Sherman, and J.E. van Lier J. Porphyrins Phthalocyanines 5 2001 161 169
14. S.-I. Ogura, K. Tabata, K. Fukushima, T. Kamachi, and I. Okura J. Porphyrins Phthalocyanines 10 2006 1116 1124
15. J.-P. Taquet, C. Frochot, V. Manneville, and M. Barberi-Heyob Curr. Med. Chem. 14 2007 1673 1687
16. Y. Zorlu, M.A. Ermeydan, F. Dumoulin, V. Ahsen, H. Savoie, and R.W. Boyle Photochem. Photobiol. Sci. 8 2009 312 318
17. A. Pashkovskaya, E. Kotova, Y. Zorlu, F. Dumoulin, V. Ahsen, I. Agapov, and Y. Antonenko Langmuir 26 2010 5726 5733
18. Y. Zorlu, F. Dumoulin, M. Durmu, and V. Ahsen Tetrahedron 66 2010 3248 3258
19. Y. Zorlu, F. Dumoulin, D. Bouchu, V. Ahsen, and D. Lafont Tetrahedron Lett. 51 2010 6615 6618
20. C.M. Allen, R. Langlois, W.M. Sharman, C. La Madeleine, and J.E. van Lier Photochem. Photobiol. 76 2002 208 216
21. +: 1093.1724; found 1093.1722.
22. +: 973.0785; found 973.0784.
23. A. Komáromi, G.L. Tolnai, and Z. Novák Tetrahedron Lett. 49 2008 7294 7298
24. 2O (5 mL) degazed under nitrogen was added, as well as the alkyne if liquid (100 μL). The nitrogen flow was maintained further 5 min, then the reaction mixture was heated overnight at 80-90 °C.
25. H. Yoshiyama, N. Shibata, T. Sato, S. Nakamura, and T. Toru Chem. Commun. 2008 1977 1979
26. E.M. Maya, P. Vazquez, and T. Torres Chem. Eur. J. 5 1999 2004 2013
27. E.M. Maya, P. Vazquez, T. Torres, L. Gobbi, F. Diederich, S. Pyo, and L. Echegoyen J. Org. Chem. 65 2000 823 830
28. E.M. Garcia-Frutos, S.M. O'Flaherty, E.M. Maya, G. de la Torre, W. Blau, P. Vazquez, and T. Torres J. Mater. Chem. 13 2003 749 753
29. S. Achelle, P. Couleaud, P. Baldeck, M.-P. Teulade-Fichou, and P. Maillard Eur. J. Org. Chem. 2011 1271 1279
30. H. Ali, P. Baillargeon, and J.E. van Lier Tetrahedron Lett. 49 2008 7253 7255
31. H. Ali, and J.E. van Lier Tetrahedron Lett. 50 2009 337 339