Highly efficient and versatile synthesis of polyarylfluorenes via Pd-catalyzed C-H bond activation

Organic Letters

Volumn 11, Issue 20, 2009, Pages 4588-4591

  Hwang, Seung Jun ^a,b   Kim, Hyun Jin ^a,b   Chang, Sukbok ^a,b  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

^b Korea Institute of Science and Technology   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 70349932317     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901854f     Document Type: Article

References (45)

1. (a)BenaiKov, M.; wudi F.; perepichka, D. F. Chem. Kev. 2004 104, 4891.
2. (b)Anthony, J. E. Chem. Rev. 2006, 106, 5028.
3. (c)Murphy, A. R.; Frechet, J. M. J. Chem. Rev. 2007, 107, 1066.
4. (a)Bernius, M. T.; Inbasekaran, M.; O'Brien, J.; Wu, W. Adv. Mater. 2000, 12, 1737.
5. (b)Scherf, U.; List, E. J. W. Adv. Mater. 2002, 14, 477.
6. (c)Morgan, L. R.; Thangaraj, K.; LeBlanc, B.; Rodgers, A.; Wolford, L. T.; Hooper, C. L.; Fan, D.; Jursic, B. S..J. Med. Chem. 2003, 46, 4552.
7. (d)Fleckenstein, C. A.; Plenio, H. Qem.-Eur. J. 2007, 13, 2701.
8. For selected recent examples, see: (a) Reisch, H.; Wiester, U.; Scherf, U.; Tuytuylkov, N. Macromolecules 1996, 29, 8240.
9. (b)Merlet, S.; Birau, M..; Wang, Z. Y. ,Org.Lett. 2002, 4, 2157.
10. (c)Wong, K.; Chi, L.; Huang, S.; Liao, Y.; Wang, L. Y. Org. Lett. 2006, 8, 5029.
11. (d)Clive, D. L. J.; Sunasee, R. Org. Lett. 2007, 9, 2677.
12. (a)Campeau, L. C.; Parisien, M.; Jean, A.; Fagnou, K. J. Am. Chem. Soc 2006, 128, 581.
13. (b)Shimizu, M.; Mochida, K.; Hiyama, T. Angew Chem., Int. Ed. 2008, 47, 9760.
14. (c)Fuchibe, K.; Akiyama, T. J. Am. Chem. Soc. 2006, 128, 1434.
15. (d)Dong, C.-G.; Hu, Q.-S. Angew. Chem., Int. Ed. 2006, l5, 2289.
16. (e)Tobisu, M.; Kita, Y.; Ano, Y.; Chatani, N. J. Am. Chem. Soc. 2008, 130, 15982.
17. (a)Gorin, D. J.; Watson, I. D.; Toste, F. D. J. Am. Chem. Soc. 2008,130, 3736.
18. (b)Zhao, Y.-B.; Mariampillai, B.; Candito, D. A.; Laleu, B.; Li, M.; Lautens, M. Angew Chem., Int. Ed. 2009, 48, 1849.
19. For recent reviews on the direct C-H functionalization, see: (a) Kakiuchi, F.; Chatani, N. Adv Synth. Catal. 2003,345, 1077.
20. (b)Campeau, L.-C.; Fagnou, K. Chem Commun. 2006, 1253.
21. (c)Alberico, D.; Scott, M. E.; Lautens, M. Chem Rev. 2007, 107, 174.
22. (d)Satoh, T.; Miura, M. Chem. Lett. 2007, 36, 200.
23. (e)Seregin, I. V.; Gevorgyan, V. Chem. Soc. Rev. 2007,36, 1173.
24. (f)Daugulis, O.; Zaitsev, V. G.; Shabashov, D.; Pham, Q.-N.; Lazareva, A. Synlett. 2007, 3382.
25. (g)Pascual, S.; de Mendoza, P.; Echavarren, A. M. Org Biomol. Chem. 2007, 5, 2727.
26. (h)Li, B.-J.; Yang, S.-.D.; Shi, Z.-J. Synlett. 2008, 949.
27. (i)Hwang, S. J.; Cho, S. H.; Chang, S. J. Am. Chem. Soc. 2008, 130, 16.158.
28. (a)Liegault, B.; Renaud, J.-L.; Bruneau, C Chem. Soc. Rev 2008, 37, 290.
29. (b)Kuwano, R. Synthesis 2009, 1049.
30. For relevant examples from this laboratory, see: (a)Ko, S.; Na, Y.; Chang, S. J. Am. Chem. Soc. 2002, 124, 750.
31. (b)Lee, J. M.; Na, Y.; Han, H.; Chang, S. Chem Soc. Rev. 2004, 33, 302.
32. (c)Ko, S.; Kang, B.; Chang, S. Angew. Chem., Int. Ed. 2005, 44, 455.
33. (d)Lee, J. M.; Park, E. J.; Cho, S. H.; Chang, S. J. Am. Chem. Soc. 2008, 130, 7824.
34. (e)Cho, S. H.; Hwang, S. J.; Chang, S. J. Am.Chem. Soc. 2008, 130, 9254.
35. (f)For details, see the Supporting Information.
36. (a)Hennessy, E. J.; Buchwald, S. L. J. Am. Chem. Soc. 2003,125, 12084.
37. (b)Garcia-Cuadrado, D.; Braga, A. A. C; Maseras, F.; Echavarren, A. M. J. Am. Chem. Soc. 2006, 128, 1066.
38. For an example of stoichiometric palladium insertion into a benzylic carbon-halogen bond, see: Fitton, P.; Mckeon, J. E.; Ream, B. C. J. Chem. Soc. D 1969, 370.
39. (a)Kuwano, R.; Kondo, Y.; Matsuyama, Y. J. Am. Chem. Soc. 2003, /25, 12104.
40. (b)Lane, B. S.; Brown, M. A.; Sames, D. J. Am Chem. Soc 2005, 127, 8050.
41. (c)Seregin, L; Ryabova, V.; Gevorgyan, V. J. Am. Chem Soc. 2007, 129, 7742.
42. (d)Wang, J.-X.; McCubbin, J. A.; Jin, M.; Laufer, R. S.; Mao, Y.; Crew, A. P.; Mulvihill, M. J.; Snieckus, V. Org. Lett.. 2008, 10, 2923.
43. (a)Davies, D. L.; Donald, S. M. A.; Macgregor, S. A. J. Am. Chem, Soc 2005, 127, 13754.
44. (b)Garcia-Cuadrado, D.; de Mendoza, P.; Braga, A. A. C.; Maseras, F.; Echavarren, A. M. J. Am. Chem. Soc. 2007, 729, 6880
45. (c)Gorelsky, S. L; Lapointe, D.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 10848.