Direct synthesis of palladium porphyrins from acyldipyrromethanes

Journal of Organic Chemistry

Volumn 70, Issue 9, 2005, Pages 3500-3510

  Sharada, Duddu S ^a   Muresan, Ana Z ^a   Muthukumaran, Kannan ^a   Lindsey, Jonathan S ^a  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCHEMISTRY; CONDENSATION; METHANE; OXIDATION; PALLADIUM COMPOUNDS; PHOTOSENSITIZERS; REDUCTION; SYNTHESIS (CHEMICAL);

LUMINESCENT AGENTS; MATERIALS CHEMISTRY; PALLADIUM PORPHYRINS; REFLUXING ETHANOLS;

PORPHYRINS;

ACYLDIPYRROMETHANE; ALCOHOL; ALKANE DERIVATIVE; CHELATE; PALLADIUM COMPLEX; PALLADIUM PORPHYRIN; PHOTOSENSITIZING AGENT; PORPHYRINOGEN; PROTON; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; ELECTRON; OXIDATION; POLYMERIZATION; REDUCTION; SYNTHESIS;

CATALYSIS; INDICATORS AND REAGENTS; LUMINESCENT AGENTS; METALLOPORPHYRINS; METHANE; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PALLADIUM; PYRROLES;

EID: 17744391810     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050120v     Document Type: Article

References (44)

1. (a) Perry, C. L.; Weber, J. H. J. Inorg. Nucl. Chem. 1971, 33, 1031-1039.
2. (b) Mehta, P.; Mehta, R. K. J. Indian Chem. Soc. 1984, LXI, 571-572.
3. (c) Adams, H.; Bailey, N. A.; Fenton, D. E.; Moss, S.; Rodriguez de Barbarin, C. O.; Jones, G. J. Chem. Soc., Dalton Trans. 1986, 693-699.
4. (d) Tayim, H. A.; Salameh, A. S. Polyhedron 1986, 5, 687-689
5. (e) Kanungo, P. K.; Sankhla, N. K.; Mehta, R. K. J. Indian Chem. Soc. 1986, LXIII, 335-336.
6. (f) Birdsall, W. J.; Weber, B. A.; Parvez, M. Inorg. Chim. Acta 1992, 196, 213-220.
7. (g) Hübler, K.; Hübler, U. Z. Anorg. Allg. Chem. 2000, 626, 1224-1236.
8. Muthukumaran, K.; Ptaszek, M.; Noll, B.; Scheidt, W. R.; Lindsey, J. S. J. Org. Chem. 2004, 69, 5354-5364.
9. (a) Eastwood, D.; Gouterman, M. J. Mol. Spectrosc. 1970, 35, 359-375.
10. (b) Callis, J. B.; Gouterman, M.; Jones, Y. M.; Henderson, B. H. J. Mol. Spectrosc. 1971, 39, 410-420.
11. Papkovsky, D. B.; O'Riordan, T.; Soini, A. Biochem. Soc. Trans. 2000, 28, 74-77.
12. Borisov, S. M.; Vasil'ev, V. V. J. Anal. Chem. 2004, 59, 155-159.
13. Wiehe, A.; Stollberg, H.; Runge, S.; Paul, A.; Senge, M. O.; Röder, B. J. Porphyrins Phthalocyanines 2001, 5, 853-860.
14. Kim, K.; Fancy, D. A.; Carney, D.; Kodadek, T. J. Am. Chem. Soc. 1999, 121, 11896-11897.
15. Thomas, D. W.; Martell, A. E. J. Am. Chem. Soc. 1959, 81, 5111-5119.
16. Buchler, J. W. In Porphyrins and Metalloporphyrins; Smith, K. M., Ed.; Elsevier Scientific Publishing Co.: Amsterdam, 1975; pp 157-231.
17. Laha, J. K.; Dhanalekshmi, S.; Taniguchi, M.; Ambroise, A.; Lindsey, J. S. Org. Process Res. Dev. 2003, 7, 799-812.
18. Rao, P. D.; Littler, B. J.; Geier, G. R., III; Lindsey, J. S. J. Org. Chem. 2000, 65, 1084-1092.
19. Zaidi, S. H. H.; Muthukumaran, K.; Tamaru, S.-I.; Lindsey, J. S. J. Org. Chem. 2004, 69, 8356-8365.
20. Srinivasan, N.; Haney, C. A.; Lindsey, J. S.; Zhang, W.; Chait, B. T. J. Porphyrins Phthalocyanines 1999, 3, 283-291.
21. Nishimura, T.; Uemura, S. Synlett 2004, 201-216.
22. Stoltz, B. M. Chem. Lett. 2004, 33, 362-367.
23. Stahl, S. S. Angew. Chem., Int. Ed. 2004, 43, 3400-3420.
24. Araki, M.; Sakata, S.; Takei, H.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1974, 47, 1777-1780.
25. Imamoto, T.; Kodera, M.; Yokoyama, M. Synthesis 1982, 134-136.
26. Rao, P. D.; Dhanalekshmi, S.; Littler, B. J.; Lindsey, J. S. J. Org. Chem. 2000, 65, 7323-7344.
27. Brückner, C.; Posakony, J. J.; Johnson, C. K.; Boyle, R. W.; James, B. R.; Dolphin, D. J. Porphyrins Phthalocyanines 1998, 2, 455-465.
28. (a) Kadish, K. M.; Araullo-McAdams, C.; Han, B. C.; Franzen, M. M. J. Am. Chem. Soc. 1990, 112, 8364-8368.
29. (b) Battioni, P.; Brigaud, O.; Desvaux, H.; Mansuy, D.; Traylor, T. G. Tetrahedron Lett. 1991, 32, 2893-2896.
30. Honeybourne, C. L.; Hill, C. A. S. J. Phys. Chem. Solids 1998, 49, 315-321.
31. Yu, L.; Muthukumaran, K.; Sazanovich, I. V.; Kirmaier, C.; Hindin, E.; Diers, J. R.; Boyle, P. D.; Bocian, D. F.; Holten, D.; Lindsey, J. S. Inorg. Chem. 2003, 42, 6629-6647.
32. (a) Jones, R. A.; Laslett, R. L. Aust. J. Chem. 1964, 17, 1056-1058.
33. (b) Nicolaou, K. C.; Claremon, D. A.; Papahatjis, D. P. Tetrahedron Lett. 1981, 22, 4647-4650.
34. Tamaru, S.-I.; Yu, L.; Youngblood, W. J.; Muthukumaran, K.; Taniguchi, M.; Lindsey, J. S. J. Org. Chem. 2004, 69, 765-777.
35. Murov, S. L.; Carmichael, I.; Hug, G. L. Handbook of Photochemistry, 2nd ed.; Marcel Dekker: New York, 1993; p 290.
36. Adler, A. D.; Longo, F. R.; Shergalis, W. J. Am. Chem. Soc. 1964, 86, 3145-3149.
37. Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2003, 125, 9578-9579.
38. Brown, W. H.; French, W. N. Can. J. Chem. 1958, 36, 371-377.
39. Littler, B. J.; Miller, M. A.; Hung, C.-H.; Wagner, R. W.; O'Shea, D. F.; Boyle, P. D.; Lindsey, J. S. J. Org. Chem. 1999, 64, 1391-1396.
40. Geier, G. R., III; Callinan, J. B.; Rao, P. D.; Lindsey, J. S. J. Porphyrins Phthalocyanines 2001, 5, 810-823.
41. Hong, S.-J.; Ka, J.-W.; Won, D.-H.; Lee, C.-H. Bull. Korean Chem. Soc. 2003, 24, 661-663.
42. Král, V.; Sessler, J. L.; Zimmerman, R. S.; Seidel, D.; Lynch, V.; Andrioletti, B. Angew. Chem., Int. Ed. 2000, 39, 1055-1058.
43. (a) Badger, G. M.; Jones, R. A.; Laslett, R. L. Aust. J. Chem. 1964, 17, 1028-1035.
44. (b) Barnett, G. H.; Hudson, M. F.; Smith, K. M. J. Chem. Soc., Perkin Trans. 1 1975, 1401-1403.