Regioselective oxidative liberation of aryl-substituted tripyrrinone metal complexes from N-confused porphyrin

Organic Letters

Volumn 4, Issue 2, 2002, Pages 181-184

  Furuta, Hiroyuki ^a,b   Maeda, Hiromitsu ^b   Osuka, Atsuhiro ^b  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BILE PIGMENT; COPPER; ORGANOMETALLIC COMPOUND; PORPHYRIN; PYRROLE DERIVATIVE; TETRAPHENYLPORPHYRIN;

ARTICLE; CHEMISTRY; METABOLISM; OXIDATION REDUCTION REACTION; SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

BILE PIGMENTS; COPPER; CRYSTALLOGRAPHY, X-RAY; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; PORPHYRINS; PYRROLES; SPECTRUM ANALYSIS;

EID: 0037165420     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0168521     Document Type: Article

References (35)

1. Falk, H. The Chemistry of Linear Oligopyrroles and Bile Pigments; Springer-Verlag: Vienna, 1989.
2. Schmid, R.; Mcdonagh, A. F. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1979; Vol. VI, p 257.
3. Kräutler, B.; Matile, P. Acc. Chem. Res. 1999, 32, 35.
4. Cavaleiro, J. A. S.; Neves, M. G. P. S.; Hewlins, M. J. E.; Jackson, A. H. J. Chem. Soc., Perkin Trans, 1 1990, 1937.
5. Fuhrhop, J.-H.; Wasser, P. K. W.; Subramanian, J.; Schrader, U. Liebigs Ann. Chem. 1974, 1450.
6. (a) Balch, A. L.; Mazzanti, M.; Noll, B. C.; Olmstead, M. M. J. Am. Chem. Soc. 1994, 116, 9114.
7. (b) Koemer, R.; Olmstead, M. M.; Ozarowski, A.; Balch, A. L. Inorg. Chem. 1999, 38, 3262.
8. Khoury, R. G.; Senge, M. O.; Colchester, J. E.; Smith, K. M. J. Chem. Soc., Dalton Trans. 1996, 3937.
9. Jeandon, C.; Krattinger, B.; Ruppert, R.; Callot, H. J. Inorg. Chem. 2001, 40, 3149.
10. (a) Funita, H.; Asano, T.; Ogawa, T. J. Am. Chem. Soc. 1994, 116, 767.
11. (b) Chmielewski, P. J.; Latos-Grazyriski, L.; Rachlewicz, K.; Glowiak, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 779.
12. (c) Latos-Grazyriski, L. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, 1999; Vol. 2, Chapter 14.
13. (a) (Ni) Chmielewski, P. J.; Latos-Grazyriski, L.; Glowiak, T. J. Am. Chem. Soc. 1996, 118, 5690.
14. (b) Chmielewski, P. J.; Latos-Grazyriski, L. Inorg. Chem. 1997, 36, 840.
15. (Ag) Furuta, H.; Ogawa, T.; Uwatoko, Y.; Araki, K. Inorg. Chem. 1999, 38, 2676.
16. (a) (Pd) Furuta, H.; Kubo, N.; Maeda, H.; Ishizuka, T.; Osuka, A.; Nanami, H.; Ogawa, T. Inorg. Chem. 2000, 39, 5424.
17. (b) Furuta, H.; Maeda, H.; Osuka, A.; Yasutake, M.; Shinmyozu, T.; Ishikawa, Y. Chem. Commun. 2000, 1143.
18. (Sb) Ogawa, T.; Furuta, H.; Takahashi, M.; Morino, A.; Uno, H. J. Organomet. Chem. 2000, 61, 551.
19. (a) (Cu) Chmielewski, P. J.; Latos-Grazyriski, L. Inorg. Chem. 2000, 40, 5475.
20. (b) Furuta, H.; Maeda, H.; Osuka, A. J. Am. Chem. Soc. 2000, 722, 803.
21. (Fe) Chen, W.-C.; Hung, C.-H. Inorg. Chem. 2001, 40, 5070.
22. (Rh) Srinivasan, A.; Furuta, H.; Osuka, A. Chem. Commun. 2001, 1666.
23. (a) Sessler, J. L.; Gebauer, A.; Král, V.; Lynch, V. Inorg. Chem. 1996, 35, 6636.
24. (b) Bröring, M.; Brandt, C. D. Chem. Commun. 2001, 499.
25. II = 2.21. We thank Prof. Y. Ishikawa at Oita University for the help of the ESR measurements.
26. 3, Z = 4, R = 0041, wR = 0.047, GOF = 0.05 for 2602 reflections with I > 3.0σ(I).
27. Heischer, E. B. J. Am. Chem. Soc. 1963, 85, 1353.
28. Similar coplanarity of the benzoyl group was also observed in Ni(II) and Cu(II) complex of 2 (R = n-butyl). See ref 8.
29. 2. The position of the meso-pyridine was determined by the ROESY spectrum. Furuta, H.; Ishizuka, T.; Osuka A.; Uwatoko, Y.; Ishikawa, Y. Angew. Chem., Int. Ed. 2001, 40, 2323.
30. 1H NMR spectrum was obtained after changing to the Ni(II) complex.
31. [2 + 2] cycloaddition mechanism was suggested in the ring opening by photo-oxidation of bacteriochlorophyll derivatives. Brown, S. B.; Smith, K. M.; Bisset, G. M. F.; Troxler, R. F. J. Biolog. Chem. 1980, 255, 8063.
32. The low oxidation potential value of 390 mV for the Cu(III)/Cu(II) couple of NCTPP-Cu(II) was reported. See ref 14a.
33. The relative energy of inner core tautomers of 3 was estimated by DFT calculation (B3LYP/6-31G** level). The tautomeric form of 3 in Scheme 4 is the most stable by 7.78-22.15 kcal/mol compared to the other tautomers. See Supporting Information.
34. The ionic radii of group 10 metals were reported as follows: Ni(II) 0.63 Å, Pd(II) 0.78 Å, and Pt(II) 0.74 Å. Cotton, F. A.; Wilkinson, G.; Nurillo, C. A.; Bochmann, M. Advanced Inorganic Chemistry, 6th ed.; Wiley: New York, 1999; p 1304.
35. Visser, H. C.; Reinhoudt, D. N.; de Jong, F. Chem. Soc. Rev. 1994, 23, 75.