The intermolecular Pauson-Khand reaction of meso-substituted porphyrins

European Journal of Organic Chemistry

Volumn , Issue 29, 2008, Pages 4881-4890

  Horn, Sabine ^a   Senge, Mathias O ^a  

^a TRINITY COLLEGE DUBLIN   (Ireland)

Author keywords

Cyclizations; Intermolecular reactions; Pauson Khand reaction; Porphyrin dimers; Porphyrins

Indexed keywords

EID: 53849114718     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800488     Document Type: Article

References (43)

1. I. U. Khand, G. R. Knox, P. L. Pauson, W. E. Watts, J. Chem. Soc., Chem. Commun. 1971, 36.
2. S. E. Gibson, N. Mainolfi, Angew. Chem. Int. Ed. 2005, 44, 3022-3027.
3. P. Magnus, L.-M. Principe, Tetrahedron Lett. 1985, 26, 4851-4854.
4. P. Magnus, C. Exon, P. Albaugh-Robertson, Tetrahedron 1985, 41, 5861-5869.
5. F. Marks, G. Fürstenberger in Prostaglandins, Leukotrienes, and Other Eicosanoids: From Biogenesis to Clinical Application, Wiley-VCH, Weinheim, 1999.
6. D. S. Straus, C. K. Glass, Med. Res. Rev. 2001, 21, 185-210.
7. N. E. Schore, M. C. Croudace, J. Org. Chem. 1981, 46, 5436-5438.
8. J. Blanco-Urgoiti, L. Anorbe, L. Pérez-Serrano, G. Domínguez, J. Pérez-Castells, Chem. Soc. Rev. 2004, 33, 32-42.
9. a) M. O. Senge, Acc. Chem. Res. 2005, 38, 733-743;
10. b) S. Horn, N. N. Sergeeva, M. O. Senge, J. Org. Chem. 2007, 72, 5414-5417;
11. c) K. Dahms, M. O. Senge, M. B. Bakar, Eur. J. Org. Chem. 2007, 3833-3848.
12. M. O. Senge, J. Richter, J. Porphyrins Phthalocyanines 2004, 8, 934-953.
13. a) M. Séverac, L. Le Pleux, A. Scarpaci, E. Blart, F. Odobel, Tetrahedron Lett. 2007, 48, 6518-6522;
14. b) C. Maeda, S. Yamaguchi, C. Ikeda, H. Shinokubo, A. Osuka, Org. Lett. 2008, 10, 549-552.
15. I. U. Khand, P. L. Pauson, J. Chem. Res. (S) 1977, 1, 9;
16. I. U. Khand, P. L. Pauson, J. Chem. Res. (M) 1977, 168-187.
17. S. G. DiMagno, S.-Y. Lin, M. J. Therien, J. Org. Chem. 1993, 58, 5983-5993.
18. J. W. Buchler in Porphyrins and Metalloporphyrins (Ed.: K. M. Smith), Elsevier Scientific Publishing Company, Amsterdam, 1975, p. 177-187.
19. S. Laschat, A. Becheanu, T. Bell, A. Baro, Synlett 2005, 17, 2547-2570.
20. a) K. M. Brummond, D. P. Curran, B. Mitasev, S. Fischer, J. Org. Chem. 2005, 70, 1745-1753;
21. b) H. Coa, S. G. Van Ornum, J. Deschamps, J. Flippen-Anderson, F. Laib, J. M. Cook, J. Am. Chem. Soc. 2005, 127, 933-943.
22. M. E. Krafft, I. L. Scott, R. H. Romero, S. Feibelmann, C. E. Van Pelt, J. Am. Chem. Soc. 1993, 115, 7199-7207.
23. G. Domínguez, L. Casarrubios, J. Rodríguez-Noriega, J. Pérez-Castells, Helv. Chim. Acta 2002, 85, 2856-2861.
24. This intermediate could also not been isolated by Magnus et al., who postulated the reaction mechanism: P. Magnus, L. M. Principe, Tetrahedron Lett. 1985, 26, 4851-4854;
25. thus far it has only been detected by mass spectrometry: Y. Gimbert, D. Lesage, A. Milet, F. Fournier, A. E. Greene, J.-C. Tabet, Org. Lett. 2003, 5, 4073-4075.
26. L. V. R. Bonaga, M. E. Krafft, Tetrahedron 2004, 60, 9795-9833.
27. Y. K. Chung, B. Y. Lee, N. Jeong, M. Hundecek, P. L. Pauson, Organometallics 1993, 12, 220.
28. P. L. Pauson in Organometallics in Organic Synthesis Aspects of a Modern Interdisciplinary Field (Eds.: A. de Meijere, H. tom Dieck), Springer, Berlin, 1988, p. 233.
29. I. U. Khand, E. Murphy, P. L. Pauson, J. Chem. Res. (M) 1978, 4434-4453;
30. I. U. Khand, E. Murphy, P. L. Pauson, J. Chem. Res. (S) 1978, 350-351.
31. T. J. de Bruin, A. Milet, A. E. Greene, Y. Gimbert, J. Org. Chem. 2004, 69, 1075-1080.
32. J. Subramanian, J. H. Fuhrhop in The Porphyrins (Ed.: D. Dolphin), Academic Press, New York, 1978, vol. 2, pp. 255-285.
33. a) M. O. Senge, X. Feng, Tetrahedron Lett. 1999, 40, 4165-4168;
34. b) X. Feng, M. O. Senge, J. Chem. Soc. Perkin Trans. 1 2001, 1030-1038.
35. a) I. U. Khand, G. R. Knox, P. L. Pauson, W. E. Watts, M. I. Foreman, J. Chem. Soc. Perkin Trans. 1 1973, 977-981;
36. b) I. U. Khand, P. L. Pauson, J. Chem. Soc. Perkin Trans. 1 1976, 30-32;
37. c) S. MacWhorther, V. Sampath, M. M. Olmstead, N. E. Schore, J. Org. Chem. 1988, 53, 203;
38. d) J. L. Arias, A. Cabrera, P. Sharma, N. Rosas, R. Sampere, J. Mol. Catal. A 2006, 246, 237-241;
39. e) R. Cabot, A. Lledó, M. Revés, A. Riera, X. Verdaguer, Organometallics 2007, 26, 1134-1142.
40. I. U. Khand, G. R. Knox, P. L. Pauson, W. E. Watts, M. I. Foreman, J. Chem. Soc. Perkin Trans. 1 1973, 977-981.
41. a) A. Wiehe, Y. M. Shaker, J. C. Brandt, S. Mebs, M. O. Senge, Tetrahedron 2005, 61, 5535-5564;
42. b) A. Berlicka, L. Latos-Grazynski, T. Lis, Inorg. Chem. 2005, 44, 4522-4533.
43. K. Tomazaki, A. B. Lysenko, M. Taniguchi, J. S. Lindsey, Tetrahedron 2004, 60, 2011-2023.