First synthesis of perfluorinated corrole and its Mn=O complex

Organic Letters

Volumn 5, Issue 5, 2003, Pages 617-620

  Liu, Hai Yang ^a   Lai, Tat Shing ^a   Yeung, Lam Lung ^a   Chang, Chi K ^a  

^a HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

2,3,7,8,12,13,17,18 OCTAFLUORO 5,10,15 TRIS(PENTAFLUOROPHENYL)CORROLE; ALKENE DERIVATIVE; BENZENE DERIVATIVE; MANGANESE DERIVATIVE; OXYGEN DERIVATIVE; PERFLUORO COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; COMPLEX FORMATION; DRUG SYNTHESIS; ELECTRON; FLUORINATION; IRRADIATION; MOLECULAR STABILITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION REDUCTION REACTION; RADIOSENSITIVITY; STRUCTURE ANALYSIS;

EID: 0141629868     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol027111i     Document Type: Article

References (55)

1. Paolesse, R. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic: San Diego, CA, 2000; Vol. 2, Chapter 11, p 201-232.
2. (a) Meier-Callahan, A. E.; Gray, H. B.; Gross, Z. Inorg. Chem. 2000, 39, 3605.
3. (b) Gross, Z.; Golubkov, G.; Simkhovich, L. Angew. Chem., Int. Ed. 2000, 39, 4045.
4. (c) Vogel, E.; Will, S.; Tilling, A. S.; Neumann, L.; Lex, J.; Bill, E.; Trautwein, A. X.; wieghart, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 731.
5. (d) Will, S.; Lex, J.; Vogel, E.; Adamian, V. A.; Caemelbecke, E. V.; Kadish, K. M. Inorg. Chem. 1996, 35, 5577.
6. (e) Will, S.; Lex, J.; Vogel, E.; Schmickler, H.; Gisselbrecht, J.-P.; Haubtmann, C.; Bernard, M.; Gross, M. Angew. Chem., Int. Ed. 1997, 36, 357.
7. Paolesse, R.; Natale, C. D.; Macognano, A.; Sagone, F.; Scarselli, M. A. ; Chiaradia, P.; Troitsky, V. I.; Berzina, T. S.; D'Amico, A. Langmuir 1999, 15, 1268.
8. (a) Gross, Z.; Simkhovich, L.; Galili, N. Chem. Commun. 1999, 599.
9. (b) Simkhovich, L.; Mahammed, A.; Goldberg, I.; Gross, Z. Chem. Eur. J. 2001, 7, 1041.
10. (c) Grodkowski, J.; Neta, P.; Fujita, E.; Mahammed, A.; Simkhovich, L.; Gross, Z. J. Phys. Chem. A 2002, 106, 4772.
11. Aviezer, D.; Cotton, S.; David, M.; Segev, A.; Khaselev, N.; Galili, N.; Gross, Z.; Yayon, A. Cancer Res. 2000, 60, 2973.
12. (a) Paolesse, R.; Pandey, R. K.; Forsyth, T. P.; Jaquinod, L.; Gerzevske, K. R.; Nurco, D. J.; Senge, M. O.; Licoccia, S.; Boshi, T.; Smith, K. M. J. Am. Chem. Soc. 1996, 118, 3869.
13. (b) Jérome, F.; Gros, C. P.; Tardieux, C.; Barbe, J.-M.; Guilard, R. Chem. Commun. 1998, 2007.
14. (a) Gryko, D. T. Eur. J. Org. Chem. 2002, 1735.
15. (b) Simkhovich, L.; Iyer, P.; Goldberg, I.; Gross, Z. Chem. Eur. J. 2002, 8, 2595.
16. (c) Andrioletti, B.; Rose, E. J. Chem. Soc., Perkin Trans. 1 2002, 715.
17. (d) Harmer, J.; Doorslaer, S. V.; Gromov, I.; Broring, M.; Jeschke, G.; Schweiger, A. J. Phys. Chem. B 2002, 106, 2801.
18. (e) Gryko, D. T.; Jadach, K. J. Org. Chem. 2001, 66, 4267.
19. (f) Bröring, M.; Hell, C. Chem. Commun. 2001, 2336.
20. (g) Jérôme, F.; Barbe, J.-M.; Gros, C. P.; Guilard, R.; Fischer, J.; Weiss, R. New J. Chem. 2001, 25, 93.
21. (h) Furuta, H.; Maeda, H.; Osuka, A. J. Am. Chem. Soc. 2001, 123, 6435.
22. (i) Steene, E.; Wondimagegn, T.; Ghosh, A. J. Phys. Chem. B 2001, 105, 11406.
23. (j) Bendix, J.; Dmochowski, I. J.; Gray, H. B.; Mahammed, A.; Simkhovich, L.; Gross, Z. Angew. Chem., Int. Ed. 2000, 39, 4048.
24. (k) Simkhovich, L.; Galili, N.; Saltsman, I.; Goldberg, I.; Gross, Z. Inorg. Chem. 2000, 39, 2704.
25. (l) Gryko, D. T. Chem. Commun. 2000, 2243.
26. (m) Kadish, K. M.; Erben, C.; Ou, Z. P.; Adamian, V. A.; Will, S.; Vogel, E. Inorg. Chem. 2000, 39, 3312.
27. (n) Jérôme, F.; Billier, B.; Barbe, J.-M.; Espinosa, E.; Dahaoui, S.; Lecomte, C.; Guilard, R. Angew. Chem., Int. Ed. 2000, 39, 4051.
28. Ochsenbein, P.; Ayougou, K.; Mandon, D.; Fischer, J.; Weiss, R.; Austin, R. N.; Jayaraj, K.; Gold, A.; Terner, J.; Fajer, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 348.
29. Bhyrappa, P.; Chrshnan, V. Inorg. Chem. 1991, 30, 239.
30. Wijeskera, T.; Matsumoto, A.; Dolphin, D.; Lexa, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 1028.
31. Grinstaff, M. W.; Hill, M. F.; Birnbaum, E. R.; Schaefer, W. P.; Labinger, J. A.; Gray, H. B. Inorg. Chem. 1995, 34, 4896.
32. Chang, C. K.; Ebina, F. J. Chem. Soc. Chem., Commun. 1981, 778.
33. (a) Ellis, P. E.; Lyons, J. W. Coord. Chem. Rew. 1990, 105, 185.
34. (b) Ellis, P. E.; Lyons, J. E. Catal. Lett. 1989, 3, 389.
35. (c) Grinstaff, M. W.; Hill, M. G.; Labinger, J. A.; Gray, H. B. Science 1994, 264, 1311.
36. (d) Dolphin, D.; Traylor, T. G.; Xie, L. Y. Acc. Chem. Res. 1997, 30, 251.
37. Leroy, J.; Bondon, A.; Toupet, L.; Rolando, C. Chem. Eur. J. 1997, 3, 1890.
38. Woller, E. K.; DiMagno, S. G. J. Org. Chem. 1997, 62, 1588.
39. (a) Porhiel, E.; Bondon, A.; Leroy, J. Tetrahedron Lett. 1998, 39, 4829.
40. (b) Porhiel, E.; Bondon, A.; Leroy, J. Eur. J. Inorg. Chem. 2000, 1097.
41. (a) Bench, B. A.; Beveridge, A.; Sharman, W. M.;. Diebold, G. J.; van Lier, J. E. and Gorun, S. M. Angew. Chem., Int. Ed. 2002, 41, 748.
42. (b) Bench, B. A.; Brennessel, W. W.; Lee, H.-J.; Gorun, S. M. Angew. Chem., Int. Ed. 2002, 41, 750.
43. (c) Jones, J. G.; Twigg, M. V. Inorg. Chem. 1969, 8, 2018.
44. (d) Birchall, J. M.; Haszeldine, R. N. Morley, J. O. J. Chem. Soc. C 1970, 2667.
45. Golubkov, G.; Bendix, J.; Gray, H. B.; Mahammed, A.; GoldBerg, I.; DiBilio, A. J.; Gross, Z. Angew. Chem., Int. Ed. 2001, 40, 2132.
46. Paolesse, R.; Nardis, S.; Sagone, F.; Khoury, R. G. J. Org. Chem. 2001, 66, 550.
47. (a) Gross, Z.; Galili, N.; Saltsman, I. Angew. Chem., Int. Ed. Engl. 1999, 38, 1427.
48. (b) Gross, Z.; Galili, N.; Simkhovich, L.; Saltsman, I.; Botoshansky, M. ; Bläser, D.; Boese, R.; Goldberg, I. Org. Lett. 1999, 599.
49. Woller, E. K.; Smirnov, V. V.; DiMagno, S. G. J. Org. Chem., 1998, 63, 5706.
50. max 395.0, 570.0 nm.
51. Dolphin, D.; Johnson, A. W.; Leng, J.; Van den Broek, P. J. Chem. Soc. C 1966, 880.
52. Kadish, K. M.; Adamian, V. A.; Caemelbecke, E. V.; Gueletii, E.; Will, S.; Erben, C.; Vogel, E. J. Am. Chem. Soc. 1998, 120, 11986.
53. To directly compare the robustness of the two catalysts, we did a comparison in neat cyclohexene: catalyst (1.2 μmol) in cyclohexene (2 mL) at room temperature was added aliquot portions of solid PhIO (0.12 mmol) successively soon after the last portion being consumed in the solution. 2b was completely bleached after 5 portions of PhIO (giving 450 turnover), while 2a could still be recovered by more than 50% even after 10 portions of PhIO (near 1000 turnover).
54. 3, -55°C) δ -136.5 (d, J = 22.6, 2F), -137.0 (d, J = 26.0, 1 F), -137.2 (d, J = 20.9, 2F), -137.6 (d, J = 24.3, 1F), -151.1 (2t, 3F), -160.3 (m, 6F).
55. Despite the earlier conclusion that 4b is not active (ref 2b), in our study both intermediates reacted with substrates and yielded products, with 4a being much more active and thus easier to quantify within a given time frame.