N-fusion reaction sequence of heptaphyrin(1.1.1.1.1.1.1): Singly, doubly, and quadruply N-fused heptaphyrins

Chemistry - A European Journal

Volumn 12, Issue 35, 2006, Pages 9095-9102

  Saito, Shohei ^a   Osuka, Atsuhiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Boron; Conjugation; Macrocycles; N fusion reaction; Porphyrinoids

Indexed keywords

BORON; COMPLEXATION; FLUORESCENCE; INFRARED RADIATION; REACTION KINETICS; X RAY CRYSTALLOGRAPHY;

MACROCYCLES; N-FUSION REACTIONS; PORPHYRINOIDS;

AROMATIC COMPOUNDS;

EID: 33845465820     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200600671     Document Type: Article

References (47)

1. a) A. Jasat, D. Dolphin. Chem. Rev. 1997, 97, 2267:
2. b) J. L. Sessler, A. Gcbauer, S. J. Weghorn, in The Porphyrin Handbook, Vol. 2 (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, San Diego, 2000, pp. 55-124;
3. c) T. D. Lash, Angew. Chem. 2000, 112, 1833;
4. Angew. Chem. Int. Ed. 2000, 39, 1763;
5. d) H. Furuta, H. Maeda, A. Osuka, Chem. Commun. 2002, 1795;
6. e) J. L. Sessler, D. Seidel, Angew. Chem. 2003, 115, 5292;
7. Angew. Chem. Int. Ed. 2003, 42, 5134;
8. f) T. K. Chandrashekar, S. Venkatraman, Acc. Chem. Res. 2003, 36, 676;
9. g) S. Shimizu, A. Osuka, Eur. J. Inorg. Chem. 2006, 1319.
10. a) E. Vogel, M. Michels, L. Zander, J. Lex, N. S. Tuzun, K. N. Houk, Angew. Chem. 2003, 115, 2964;
11. Angew. Chem. Int. Ed. 2003, 42, 2857;
12. b) Y. Tanaka, W. Hoshino, S. Shimizu, K. Youfu, N. Aratani, N. Maruyama, S. Fujita, A. Osuka, J. Am. Chem. Soc. 2004, 126, 3046;
13. c) S. Shimizu, V. O. Anand, R. Taniguchi, K. Furukawa, T. Kato, T. Yokoyama, A. Osuka, J. Am. Chem. Soc. 2004, 126, 12280;
14. d) S. Shimizu, Y. Tanaka, K. Youfu, A. Osuka, Angew. Chem. 2005, 117, 3792;
15. Angew. Chem. Int. Ed. 2005, 44, 3726;
16. e) S. Mori, A. Osuka, J. Am. Chem. Soc. 2005, 127, 8030;
17. f) V. G. Anand, S. Saito, S. Shimizu, A. Osuka, Angew. Chem. 2005, 117, 7410;
18. Angew. Chem. Int. Ed. 2005, 44, 7244.
19. a) M. G. P. M. S. Neves, R. M. Martins, A. C. Tomé, A. J. D. Silvestre, A. M. S. Silva, V. Félix, M. G. B. Drew, J. A. S. Cavaleiro, Chem. Commun. 1999, 385;
20. b) J.-Y. Shin, H. Furuta, A. Osuka, Angew. Chem. 2001, 113, 639;
21. Angew. Chem. Im. Ed. 2001, 40, 619;
22. c) J.-Y. Shin, H. Furuta, K. Yoza, S. Igarashi, A. Osuka, J. Am. Chem. Soc. 2001, 123, 7190.
23. a) H. Furuta, T. Ishizuka, A. Osuka, T. Ogawa, J. Am. Chem. Soc. 1999, 121, 2945;
24. b) H. Furuta, T. Ishizuka, A. Osuka, T. Ogawa, J. Am. Chem. Soc. 2000, 122, 5748;
25. c) A. Srinivasan, T. Ishizuka, H. Furuta, Angew. Chem. 2004, 116, 894;
26. Angew. Chem. Int. Ed. 2004, 43, 876.
27. a) S. Shimizu, J.-Y. Shin, H. Furuta, R. Ismacl, A. Osuka, Angew. Chem. 2003, 115, 82:
28. Angew. Chem. Int. Ed. 2003, 42, 78;
29. b) S. Mori, J.-Y. Shin, S. Shimizu, F. Ishikawa, H. Furuta, A. Osuka, Chem. Eur. J. 2005, 11, 2417;
30. c) M. Suzuki, R. Taniguchi, A. Osuka, Chem. Commun. 2004, 2682.
31. C.-H. Hung, J.-P. Jong, M.-Y. Ho, G.-H. Lee, S.-M. Peng, Chem. Eur. J. 2002, 8, 4542.
32. R. Guilard, D. T. Gryko, G. Canard, J.-M. Barbc, B. Koszarna, S. Brandes, M. Tasior, Org. Lett. 2002, 4, 4491.
33. w= 0.2235 (all data), GOF = 1.186 [I> 2.0σ(I)].
34. w = 0.2558 (all data), GOF = 1.154 [I> 2.0σ(I)].
35. This reaction conditions were used for the preparations of hexapyr-rolylbenzene: H. A. M. Biemans, C. Zhang, P. Smith, H. Kooijman, W. J. J. Smeets, A. L. Spek, E. W. Meijer, J. Org. Chem. 1996, 61, 9012.
36. A. Werner, M. Michels, L. Zander, J. Lex, E. Vogel, Angew. Chem. 1999, 111, 3866:
37. Angew. Chem. Int. Ed. 1999, 38, 3650.
38. w = 0.2969 (all data), GOF= 1.026 [I>2.0σ(I)].
39. a) C. G. Ciaessens, D. González-Rodríguez, T. Torres, Chem. Rev. 2002, 102, 835;
40. b) Y. Inokuma, J. H. Kwon, T. K. Ahn, M.-C. Yoo, D. Kim, A. Osuka, Angew. Chem. 2006, 118, 975;
41. Angew. Chem. Int. Ed. 2006, 45, 961.
42. a) W. J. Belcher, P. D. W. Boyd, P. J. Brothers, M. J. Liddell, C. E. F. Rickard, J. Am. Chem. Soc. 1994, 116, 8416;
43. b) W. J. Belcher, M. Breede, P. J. Brothers, C. E. F. Rickard, Angew. Chem. 1998, 110, 1133;
44. Angew. Chem. Int. Ed. 1998, 37, 1112;
45. c) A. Weiss, H. Pritzkow, P. J. Brothers, W. Siebert, Angew. Chem. 2001, 113, 4311;
46. Angew. Chem. Int. Ed. 2001, 40, 4182;
47. d) T. Köhler, M. C. Hodgson, D. Seidel, J. M. Veauthier, S. Meyer, V. Lynch, P. D. W. Boyd, P. J. Brothers, J. L. Sessler, Chem. Commun. 2004, 1060.