Synthesis of arylated perylene bisimides through C - H bond cleavage under ruthenium catalysis

Organic Letters

Volumn 11, Issue 23, 2009, Pages 5426-5429

  Nakazono, Satomi ^b   Easwaramoorthi, Shanmugam ^c   Kim, Dongho ^c   Shinokubo, Hiroshi ^a   Osuka, Atsuhiro ^b  

^a NAGOYA UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

^c Yonsei University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 72449190088     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol902271b     Document Type: Article

References (38)

1. (a) Herrmann, A.; Müllen, K. Chem Lett. 2006, 35, 978.
2. (b) Würthner, F. Chem. Commun. 2004, 1564.
3. (c) Wasielewski, M, R. J. Org. Chem. 2006, 71, 5051.
4. (d) Langhals, H. Helv. Chim. Acta 2005, 88, 1309.
5. (e) Langhals, H. Heterocycles 1995, 40, 477.
6. (f) Langhals, H. Molecular Devices. Chiral, Bichromophoric Silicones: Ordering Principles in Complex Molecules in Silicon Based Polymers; Ganachaud, F.,; Boileau, S.,; Boury, B., Eds.; Springer, 2008; p 51.
7. Nakazono, S.; Imazaki, Y.; Yoo, H.; Yang, J.; Sasamori, T.; Tokitoh, N.; Cedric, T.; Kageyama, H.; Kim, D.; Shinokubo, H.; Osuka, A. Chem - Eur. J. 2009, 15, 7530.
8. We have presented these results at the 55th Symposium, on Organometallic Chemistry, Japan 2008. Nakazono, S.; Shinokubo, H.; Osuka, A. Abstracts of the 55th Symposium on Organometallic Chemistry, Japan 2008; p 199.
9. For selected examples on arylated PBI derivatives at bay areas, see: (a) Qiu, W.; Chen, S.; Sun, X.; Liu, Y.; Zhu, D. Org. Lett. 2006, 8, 867.
10. (b) Chao, C.-C.; Leung, M.-K.; Su, Y. O.; Chiu, K.-Y.; Lin, T.-H.; Shieh, S.-J.; Lin, S.-C. J. Org. Chem. 2005, 70, 4323.
11. (c) Sugiyasu, K.; Fujita, N.; Sinkai, S. Angew. Chem., Int. Ed. 2004, 43, 1229.
12. (d) Ahrens, M. J.; Sinks, L. E.; Rybtchinski, B.; Liu, W.; Jones, B. A.; Giaimo, J. M.; Gusev, A. V.; Goshe, A. J.; Tiede, D. M.; Wasielewski, M. R..J. Am. Chem. Soc. 2004, 126, 8284.
13. (e) Avlasevich, Y.; Müller, S.; Erk, P.; Müllen, K. Chem. - Eur. J. 2007, 13, 6555.
14. (f) Kelley, R. F.; Shin, W. S.; Rybtchinski, B.; Sinks, L. E.; Wasielewski, M. R. J. Am. Chem. Soc. 2007, 129, 3173.
15. (g) Vajiravelu, S.; Ramunas, L.; Juozas Vidas, G.; Valentas, G.; Vygintas, J.; Valiyaveettil, S. J. Mater. Chem. 2009, 19, 4268.
16. (h) Li, Y.; Zheng, H.; Li, Y.; Wang, S.; Wu, Z.; Liu, P.; Gao, Z.; Liu, H.; Zhu, D. J. Org. Chem. 2007, 72, 2878.
17. (a) Handbook of C-H Transformations; Dyker, G., Ed.; Wiley-VCH: Weinheim, 2005.
18. (b) Kakiuchi, F.; Chatani, N. Adv. Synth. Catal 2003, 345, 1077.
19. (c) Godula, K.; Sames, D. Science 2006, 312, 67.
20. (d) Activation of Unreactive Bonds and Organic Synthesis; Murai, S., Ed.; Springer: Berlin, 1999.
21. (e) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174.
22. (a) Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529.
23. (b) Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N.; Murai, S. Bull, Chem. Soc. Jpn. 1995, 68, 62.
24. (c) Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826.
25. (a) Kakiuchi, F.; Kan, S.; Igi, K.; Chatani, N.; Murai, S. J. Am. Chem Soc. 2003, 125, 1698.
26. (b) Kakiuchi, F.; Matsuura, Y.; Kan, S.; Chatani, N. J. Am. Chem, Soc. 2005, 127, 5936.
27. (c) Kitazawa, K.; Kochi, T.; Sato, M.; Kakiuchi, F. Org. Lett. 2009, 11, 1951.
28. No reaction proceeded with pentafluorophenyl and 2-thienyl boronates. The use of 1-naphthyl boronate resulted in formation of an inseparable mixture of several atropisomers in 50% yield.
29. w = 0.2335 (all data), GOF = 1.044 (I > 2.Os(I)).
30. w = 0.28.14 (all data), GOF = 1.049 (I > 2.Os(I)).
31. (a) Seisenberger, G.; Ried, M. U.; Endre, T.; Buning, H.; Hallek, M.; Brauchle, C. Science 2001, 294, 1929.
32. (b) Cotlet, M.; Hofkens, J.; Maus, M..; Gensch, T.; Van der Auweraer, M..; Michiels, J.; Dirix, G.; Van Guyse, M..; Vanderleyden, J.; Visser, A. J. W. G.; De Schryver, F. C. J. Phys. Chem. B 2001, 105, 4999.
33. (c) Margineanu, A.; Hofkens, J.; Cotlet, M.; Habuchi, S.; Stefan, A.; Qu, J.; Kohl, C.; Müllen, K.; Vercammen, J.; Engelborghs, Y.; Gensch, T.; De Schryver, F. C J. Phys. Chem. B 2004, 108, 12242.
34. (a) Qu, J.; Kohl, C.; Pottek, M.; Müllen, K. Angew. Chem., Int. Ed, 2004, 43, 1528.
35. (b) Kohl, C.; Weil, T.; Qu, J.; Müllen, K. Chem - Eur. J. 2004. 10, 5297.
36. (c) Peneva, K.; Mihov, G.; Nolde, F.; Rocha, S.; Hotta, J.; Braechmans, K.; Hofkens, J.; Uji-i, H; Herromann, A.; Müllen, K.Agnew. Chem., Int. Ed. 2008, 47, 3372.
37. Ohara, Y.; Akiba, K.; Inamoto, N. Bull. Chem. Soc. Jpn. 1983, 56, 1508.
38. w = 0.2600 (all data), GOF = 1.174 (I > 2.Os(I)).