Palladium(II)-triggered rearrangement of heptaphyrins to N-confused porphyrins

Angewandte Chemie - International Edition

Volumn 50, Issue 15, 2011, Pages 3475-3478

  Yoneda, Tomoki ^a   Saito, Shohei ^a   Yorimitsu, Hideki ^a   Osuka, Atsuhiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

heptaphyrins; metalation; palladium; porphyrinoids; rearrangement

Indexed keywords

EXPANDED PORPHYRINS; HEPTAPHYRINS; METALATION; METALATION REACTION; N-CONFUSED; N-CONFUSED PORPHYRINS; PORPHYRINOIDS; REARRANGEMENT;

PALLADIUM COMPOUNDS;

PORPHYRINS;

EID: 79953242734     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201100243     Document Type: Article

References (43)

1. J. L. Sessler, A. Gebauer, S. J. Weghorn, in The Porphyrin Handbook, Vol. 2 (Eds.:, K. M. Kadish, K. M. Smith, R. Guilard,), Academic Press, San Diego, 1999, p. 55
2. A. Jasat, D. Dolphin, Chem. Rev. 1997, 97, 2267
3. T. D. Lash, Angew. Chem. 2000, 112, 1833
4. Angew. Chem. Int. Ed. 2000, 39, 1763
5. H. Furuta, H. Maeda, A. Osuka, Chem. Commun. 2002, 1795
6. J. L. Sessler, D. Seidel, Angew. Chem. 2003, 115, 5292
7. Angew. Chem. Int. Ed. 2003, 42, 5134
8. T. K. Chandrashekar, S. Venkatraman, Acc. Chem. Res. 2003, 36, 676.
9. E. Vogel, M. Michels, L. Zander, J. Lex, N. S. Tuzun, K. N. Houk, Angew. Chem. 2003, 115, 2964
10. Angew. Chem. Int. Ed. 2003, 42, 2857.
11. Y. Tanaka, W. Hoshino, S. Shimizu, K. Youfu, N. Aratani, N. Maruyama, S. Fujita, A. Osuka, J. Am. Chem. Soc. 2004, 126, 3046
12. Y. Tanaka, H. Shinokubo, Y. Yoshimura, A. Osuka, Chem. Eur. J. 2009, 15, 5674
13. S. Saito, K. S. Kim, Z. S. Yoon, D. Kim, A. Osuka, Angew. Chem. 2007, 119, 5687
14. Angew. Chem. Int. Ed. 2007, 46, 5591
15. R. Sakamoto, S. Saito, S. Shimizu, Y. Inokuma, N. Aratani, A. Osuka, Chem. Lett. 2010, 39, 439
16. K. Moriya, S. Saito, A. Osuka, Angew. Chem. 2010, 122, 4393
17. Angew. Chem. Int. Ed. 2010, 49, 4297.
18. H. Furuta, T. Asano, T. Ogawa, J. Am. Chem. Soc. 1994, 116, 767.
19. P. J. Chmielewski, L. Latos-Grazyński, K. Rachlewicz, T. Glowlaw, Angew. Chem. 1994, 106, 805
20. Angew. Chem. Int. Ed. Engl. 1994, 33, 779.
21. P. J. Chmielewski, Angew. Chem. 2010, 122, 1399
22. Angew. Chem. Int. Ed. 2010, 49, 1359.
23. S. Saito, J.-Y. Shin, J. M. Lim, K. S. Kim, D. Kim, A. Osuka, Angew. Chem. 2008, 120, 9803
24. Angew. Chem. Int. Ed. 2008, 47, 9657
25. S. Saito, A. Osuka, Chem. Eur. J. 2006, 12, 9095
26. Y. Tanaka, S. Saito, S. Mori, N. Aratani, H. Shinokubo, N. Shibata, Y. Higuchi, Z. S. Yoon, K. S. Kim, S. B. Noh, J. K. Park, D. Kim, A. Osuka, Angew. Chem. 2008, 120, 693
27. Angew. Chem. Int. Ed. 2008, 47, 681
28. S. Saito, K. Furukawa, A. Osuka, Angew. Chem. 2009, 121, 8230
29. Angew. Chem. Int. Ed. 2009, 48, 8086
30. S. Saito, K. Furukawa, A. Osuka, J. Am. Chem. Soc. 2010, 132, 2128.
31. W=0.1387 (all data), GOF=0.939. CCDC 807128 (3), CCDC 807129 (7), and CCDC 807130 (9) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
32. For examples of this type of complex with other metals, see Ni(II) and Pt(II):a) P. J. Chmielewski, L. Latos-Grazyński, T. Glowlaw, J. Am. Chem. Soc. 1996, 118, 5690
33. I. Schmidt, P. J. Chmielewski, Chem. Commun. 2002, 92
34. I. Schmidt, P. J. Chmielewski, Z. Ciunik, J. Org. Chem. 2002, 67, 8917
35. I. Schmidt, P. J. Chmielewski, Inorg. Chem. 2003, 42, 5579
36. P. J. Chmielewski, I. Schmidt, Inorg. Chem. 2004, 43, 1885
37. P. J. Chmielewski, Inorg. Chem. 2007, 46, 1617
38. P. J. Chmielewski, Inorg. Chem. 2009, 48, 432
39. H.-W. Jiang, Q.-Y. Chen, J.-C. Xiao, Y.-C. Gu, Chem. Commun. 2009, 3732
40. P. J. Chmielewski, L. Szterenberg, M. Siczek, Chem. Eur. J. 2011, 17, 1009; Pt complex
41. D.-H. Won, M. Toganoh, H. Uno, H. Furuta, Dalton Trans. 2009, 6151.
42. A planar N-confused Pd porphyrin complex has been reported to have a relatively strong absorption coefficient:, H. Furuta, N. Kubo, H. Maeda, T. Ishizuka, A. Osuka, H. Nanami, T. Ogawa, Inorg. Chem. 2000, 39, 5424.
43. 22 fashion.