Indium triflate mediated synthesis of meso-substituted porphyrins

Synlett

Volumn , Issue 13, 2008, Pages 1953-1956

  Smith, Brendan M ^a   Kean, Suzanna D ^a,b   Wyatt, Mark F ^c   Graham, Andrew E ^a  

^a SWANSEA UNIVERSITY   (United Kingdom)

^b UNIVERSITY OF GLAMORGAN   (United Kingdom)

^c SWANSEA UNIVERSITY   (United Kingdom)

Author keywords

Catalysis; Indium salts; Lewis acids; Porphyrins; Synthesis

Indexed keywords

INDIUM TRIFLATE; MESO PORPHYRIN DERIVATIVE; PORPHYRIN DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; SYNTHESIS;

EID: 49649083135     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1077972     Document Type: Article

References (36)

1. (a) Gorski, L.; Malinowska, E.; Parzuchowski, P.; Zhang, W.; Meyerhoff, M. E. Electroanalysis 2003, 15, 1229.
2. (b) Frydman, L.; Olivieri, A. C.; Diaz, L. E.; Frydman, B.; Morin, F. G.; Mayne, C. L.; Grant, D. M.; Adler, A. D. J. Am. Chem. Soc. 1988,110, 336.
3. (c) Xie, Y. S.; Hill, J. P.; Charvet, R.; Ariga, K. J. Nanosci. Nanotechnol. 2007, 7, 2969.
4. (d) Senge, M. O.; Fazekas, M.; Notaras, E. G. A.; Blau, W. J.; Zawaddzka, M.; Locos, O. B.; Mhuircheartaigh, E. M. N. Adv. Mater. 2007,19, 2737.
5. (e) Nam, W. Acc. Chem. Res. 2007, 40, 522.
6. (f) Kim, D.; Osuka, A. Acc. Chem. Res. 2004, 37, 735.
7. (a) Wyatt, M. F.; Stein, B. K.; Brenton, A. G. J. Am. Soc. Mass Spectrom. 2006,17, 672.
8. (b) Griffiths, N. Master Thesis; Swansea University: UK, 2007.
9. (c) Wyatt, M. F.; Stein, B. K.; Brenton, A. G.; Kean, S. D.; Griffiths, N. W. manuscript in preparation.
10. Lindsey, J. S. In The Porphyrin Handbook, Vol. 1 ; Kadish, K. M.; Smith, K. M.; Guilard, R., Eds.; Academic Press: San Diego, 2000,45-118.
11. (a) Lindsey, J. S.; Schreiman, I. C.; Hsu, H. C.; Kearney, P. C.; Marguerettaz, A. M. J. Org. Chem. 1987, 52, 827.
12. (b) Johnstone, R. A. W.; Nunes, M. L. P. G.; Pereira, M. M.; Rocha Gonsalves, A. M. d.'A.; Serra, A. C. Heterocycles 1996, 43, 1423.
13. (c) Mohajer, D.; Zakavi, S.; Rayati, S.; Zahedi, M.; Safari, N.; Khavasi, H. R.; Shahbazian, S. New J. Chem. 2004, 28, 1600.
14. 2-porphyrins, see: Gryko, D. T.; Jadach, K. J. Org. Chem. 2001, 66, 4267.
15. Geier, G. R.; Ciringh, Y.; Li, F.; Haynes, D. M.; Lindsey, J. S. Org. Lett. 2000, 2, 1745.
16. Nagarajan, R.; Perumal, P. T. Tetrahedron 2002, 58, 1229.
17. (a) Chapman, C. J.; Frost, C. G.; Hartley, J. P.; Whittle, A. J. Tetrahedron Lett. 2001, 42, 773.
18. (b) Frost, C. G.; Hartley, J. P.; Whittle, A. J. Synlett 2001, 830.
19. Geier, G. R.; Callinan, J. B.; Rao, P. D.; Lindsey, J. S. J. Porphyrins Phthalocyanines 2001, 5, 810.
20. (a) Auge, J.; Lubin-Germain, N.; Uziel, J. Synthesis 2007, 1739.
21. (b) Chauhan, K. K.; Frost, C. G. J. Chem. Soc., Perkin Trans. 1 2000, 3015.
22. (c) Smith, B. M.; Graham, A. E. Tetrahedron Lett. 2006, 47, 9317.
23. (d) Smith, B. M.; Graham, A. E. Tetrahedron Lett. 2007, 48, 4891.
24. (e) Smith, B. M.; Skellam, E. J.; Oxley, S. J.; Graham, A. E. Org. Biomol. Chem. 2007, 5, 1979.
25. Frost, C. G.; Hartley, J. P.; Griffin, D. Tetrahedron Lett. 2002, 43, 4789.
26. Kumar, A.; Maji, S.; Dubey, P.; Abhilash, G. J.; Pandey, S.; Sarkar, S. Tetrahedron Lett. 2007, 48, 7287.
27. (a) Shargi, H.; Nejad, A. H. Tetrahedron 2004, 60, 1863.
28. (b) Shargi, H.; Nejad, A. H. Helv. Chim. Acta 2003, 86, 408.
29. A similar effect has previously been reported for alternate porphyrin syntheses employing electron-deficient species: (a) Ulman, A.; Fisher, D.; Ibers, J. A. J. Heterocycl. Chem. 1982,19, 409.
30. (b) Geier, G. R.; Lindsey, J. S. Tetrahedron 2004, 50, 11435.
31. Neya, S.; Funasaki, N. J. Heterocycl. Chem. 1997, 34, 689.
32. (a) Ema, T.; Senge, M. O.; Nelson, N. Y.; Ogoshi, H.; Smith, K. M. Angew. Chem., Int. Ed Engl. 1994, 33, 1879.
33. (b) Thamyongkit, P.; Speckbacher, M.; Diers, J. R.; Kee, H. L.; Kirmaier, C.; Holten, D.; Bocian, D. F.; Lindsey, J. S. J. Org. Chem. 2004, 69, 3700.
34. Rocha Gonsalves, A. M. d.'A.; Varejao, J. M. T. B.; Pereira, M. M. J. Heterocycl. Chem. 1991, 28, 635.
35. Oulmi, D.; Maillard, P.; Guerquin-Kern, J.-L.; Huel, C.; Momenteau, M. J. Org. Chem. 1995, 60, 1554.
36. Drain, C. M.; Gong, X. Chem. Commun. 1997, 2117.