Application of Ruppert’s reagent in preparing novel perfluorinated porphyrins, chlorins and bacteriochlorins

Abstract

A first report to demonstrate the utility of (trifluoromethyl)trimethylsilane as an efficient reagent for the synthesis of perfluorinated porphyrins, chlorins and bacteriochlorins is presented.

References

1. R. K. Pandey and C. K. Herman, Chem. Ind. (London), 1998, 739.
2. B. W. Henderson, D. A. Bellnier, W. R. Greco, A. Sharma, R. K. Pandey, L. A. Vaughan, K. R. Weishaupt and T. J. Dougherty, Cancer Res., 1997, 57, 4000.
3. G. K. Surya Prakash and A. K. Yudin, Chem. Rev., 1997, 97, 757.
4. Organofluorine Chemistry-Principles and Commercial Applications, R. E. Banks, B. E. Smart and J. C. Tatlow, Plenum Press, New York, 1994.
5. Fluorine-containing Molecules, Structure, Reactivity, Synthesis and Applications, ed. J. F. Liebman, A. Greenberg and W. R. Dolbier, Jr., VGH: New York, 1988.
6. (a) W. Wolf, C. A. Presant and K. L. Servis, Proc. Natl. Acad. Sci. U.S.A., 1990, 87, 492; (b) S. Ramaprasad, R. W. Hawk, A. H. Fowler, R. Pandey and Y. H. Liu, Proceedings of the Society of Magnetic Resonance, 2nd meeting, San Francisco, 1994, 3, 1348.
7. (a) M. Omote, A. Ando, T. Takagi, M. Koyama and I. Kumadaki, Tetrahedron, 1996, 44, 13961; (b) T. P. Wijesekera, Can. J. Chem., 1996, 74, 1868.
8. S. Ramaprasad and R. K. Pandey, unpublished results.
9. G. K. Surya Prakash, R. Krishnamurthi and G. A. Olah, J. Am. Chem. Soc., 1989, 111, 393.
10. I. Ruppert, K. Schlich and W. Volbach, Tetrahedron Lett., 1984, 25, 2195.
11. (a) R. K. Pandey, K. M. Smith and T. J. Dougherty, J. Med. Chem., 1990, 33, 2032; (b) F.-Y. Shiau, R. K. Pandey, S. Ramaprasad, T. J. Dougherty and K. M. Smith, J. Org. Chem., 1990, 55, 2190.
12. (a) A. N. Kozyrev, G. Zheng, E. Lazarou, T. J. Dougherty, K. M. Smith and R. K. Pandey, Tetrahedron Lett., 1997, 38, 3335; (b) G. Zheng and R. K. Pandey, unpublished results.
13. (a) S. Sotiriou and C. K. Chang, J. Am. Chem. Soc., 1988, 110, 2264; (b) R. K. Pandey, M. Isaac, I. McDonald, C. J. Medforth, M. O. Senge, T. J. Dougherty and K. M. Smith, J. Org. Chem., 1997, 62, 1463 and references therein.
14. G. Zheng, PhD Thesis, SUNY at Buffalo, January 1999.
15. R. K. Pandey, A. B. Sumlin, S. Constantine, M. Aoudia, W. R. Potter, D. A. Bellnier, B. W. Henderson, M. A. J. Rodgers, K. M. Smith and T. J. Dougherty, Photochem. Photobiol., 1996, 64, 194.
16. J. E. Lyons and P. E. Ellis, Jr., in Metalloporphyrins in Catalytic Oxidations, ed. R. Sheldon, Marcel Dekker, New York, 1994, pp. 297–324 and references therein.
17. T. P. Wijesekera and D. Dolphin, in Metalloporphyrins in Catalytic Oxidations, ed. R. Sheldon, Marcel Dekker, New York, 1994, pp. 193–239 and references therein.