New Heck-type reaction applied to the synthesis of protoporphyrin-IX derivatives

Organic Letters

Volumn 3, Issue 4, 2001, Pages 541-544

  Castella, M ^a   Calahorra, F ^a   Sainz, D ^a   Velasco, D ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

HALOGENATED HYDROCARBON; HEMIN; METALLOPORPHYRIN; PALLADIUM; PORPHYRIN; PROTOPORPHYRIN; VINYL DERIVATIVE; ZINC;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

CATALYSIS; CHROMATOGRAPHY, THIN LAYER; HEMIN; HYDROCARBONS, HALOGENATED; METALLOPORPHYRINS; MOLECULAR STRUCTURE; PALLADIUM; PORPHYRINS; PROTOPORPHYRINS; VINYL COMPOUNDS; ZINC;

EID: 0035932042     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol000370s     Document Type: Article

References (31)

1. (a) Collman, J. P.; Wagenknecht, P. S.; Hutchison, J. E. Angew. Chem., Int. Ed. Engl. 1994, 32, 1537-1554.
2. (b) Dawson, D. Y.; Brand, H.; Arnold, J. J. Am. Chem. Soc. 1994, 116, 9797-9798.
3. (c) Kim, K.-J.; Whang, D.; Kim, K.; Do, Y. Inorg. Chem. 1993, 32, 360-362.
4. (a) Groves, J. T.; Neumann, R. J. Am. Chem. Soc. 1989, 111, 2900-2909.
5. (b) Nango, M.; Mizusawa, A.; Miyake, T.; Yoshinaga, J. J. Am. Chem. Soc. 1990, 112, 1640-1643.
6. (c) Nishino, N.; Mihara, H.; Kobata, K.; Fujimoto, T. J. Chem. Soc., Chem. Commun. 1993, 162-163.
7. (a) Rimington, C.; Ršnnestad, A.; Western, A.; Moan, J. Int. J. Biochem. 1988, 20, 1139-1149.
8. (b) Rimington, C.; Ršnnestad, A.; Kongshang, M.; Moan, J.; Int. J. Biochem. 1989, 21, 1177-1182.
9. (c) Rimington, C.; Ršnnestad, A.; Kongshang, M.; Moan, J. Biochim. Biophys. Acta. 1989, 992, 241-242.
10. (d) Berean, D. B.; Bonett, R.; De Madariaga, M. A.; Molina, S.; Morg, M.; Sagristà, M. LL.; Vallès, M. A. Proc. SPIE-Int. Soc. Opt. Eng. 1997, 3191, 395-367.
11. (a) Gregg, B. A.; Fox, M. A.; Bard, A. J. J. Chem. Soc., Chem. Commun. 1987, 1134-1136.
12. (b) Gregg, B. A.; Fox, M. A.; Bard, A. J. J. Am. Chem. Soc. 1989, 111, 3024-3029.
13. (c) Gregg, B. A.; Fox, M. A.; Bard, A. J. J. Phys. Chem. 1989, 93, 4227-4234.
14. (d) Anderson, H. L.; Martin, S. J.; Bradley, D. C. Angew. Chem., Int. Ed. Engl. 1994, 33, 655-617.
15. (e) Treacher, K. E.; Clarkson, G. J.; Ali-Adib, Z.; McKeown, N. B. J. Chem. Soc., Chem. Commun. 1996, 73-75.
16. (f) Kroon, J. M.; Koehorst, R. B.; Van Dikj, M.; Sanders, G. M.; Sudhölter, E. J. R. J. Mater. Chem. 1997, 615-624.
17. (g) Fox, M. A.; Grant, J. V.; Melamed, D.; Torimoto, T.; Liu, C.-Y.; Bard, A. J. Chem. Mater. 1998, 10, 1771-1776.
18. Risch, N.; Gauler, R.; Keuper, R. Tetrahedron Lett. 1999, 40, 2925-2926
19. Gauler, R.; Risch, N. Eur. J. Org. Chem. 1998, 1193-1200.
20. Ali, H.; van Lier, J. E. Tetrahedron 1994, 50, 11933-11944.
21. Boyle, R. W.; Johnson, C. K.; Dolphin, D. J. Chem. Soc., Chem. Commun. 1995, 527-528.
22. Castella, M.; Trull, F. R.; Löpez Calahorra, L.; Velasco, D.; González, M. M.; Tetrahedron 2000, 56, 4017-4025.
23. Wagner, R. W.; Ciringh, Y.; Clausen, C.; Lindsey, J. S. Chem. Mater. 1999, 11, 2974-2983 and references therein.
24. DiMagno, S. G.; Lin, V. S.-Y.; Therien, M. J. J. Am. Chem. Soc. 1993, 115, 2513-1515
25. Snow, K. M.; Morris, I. K.; Smith, N. W.; Smith, K. M. J. Org. Chem. 1990, 55, 1231-1236.
26. Kenner, G. W.; McCombie, S. W.; Smith, K. M. Liebigs Ann. Chem. 1973, 1329-1338.
27. Fisher, H.; Orth, H. Die Chemie des Pyrrols; Akademische Verlag: Leipzig, 1973; Vol. II, part 1, p 401.
28. -1): 1559, 1409, 1096, 698.
29. 4: C, 77.60; H, 6.24; N, 7.54. Found: C, 77.35; H, 6.22; N, 7.21.
30. 6: C, 69.32; H, 5.58; N, 6.47. Found: C, 69.12; H, 5.59; N, 6.38.
31. 8: C, 77.90; H, 9.67; N, 3.78. Found: C, 77.95; H, 9.59; N, 3.88.