A facile route to benzo[a]fluorenes via a palladium-catalyzed reaction of 2-alkynylbromobenzene with 2-(2-alkynylphenyl)malonate

Advanced Synthesis and Catalysis

Volumn 354, Issue 16, 2012, Pages 3071-3077

  Luo, Yong ^a   Pan, Xiaolin ^a   Wu, Jie ^a,b  

^a FUDAN UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

2 (2 alkynylphenyl)malonates; 2 alkynylbromobenzenes; benzo a fluorenes; palladium catalyst; tandem reactions

Indexed keywords

EID: 84869070167     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201200606     Document Type: Article

References (47)

1. F. López, J. L. Mascareas, Chem. Eur. J. 2007, 13, 2172
2. T. Miura, M. Murakami, Chem. Commun. 2007, 217
3. N. Krause, C. Winter, Chem. Rev. 2011, 111, 1994
4. Z.-X. Yu, Y. Wang, Y. Wang, Chem. Asian J. 2010, 5, 1072.
5. M. Fukai, M. Tsukada, K. Miki, T. Suzuki, T. Sugita, K. Kinoshita, K. Takahashi, M. Shiro, K. Koyama, J. Nat. Prod. 2012, 75, 22
6. V. Rukachaisirikul, U. Sommart, S. Phongpaichit, N. Hutadilok-towatana, N. Rungjindamai, J. Sakayaroj, Chem. Pharm. Bull. 2007, 55, 1316
7. D. N. Quang, T. Hashimoto, M. Tanaka, M. Baumgartner, M. Stadler, Y. Asakawa, J. Nat. Prod. 2002, 65, 1869.
8. R. Tedesco, M. K. Youngman, S. R. Wilson, J. A. Katzenellenbogen, Bioorg. Med. Chem. Lett. 2001, 11, 1281
9. W. Sippl, Bioorg. Med. Chem. 2002, 10, 3741
10. S. Zhu, L. Wu, X. Huang, Org. Biomol. Chem. 2012, 10, 3696.
11. D. P. Walsh, Y.-T. Chang, Chem. Rev. 2006, 106, 2476
12. P. Arya, D. T. H. Chou, M.-G. Baek, Angew. Chem. 2001, 113, 351
13. Angew. Chem. Int. Ed. 2001, 40, 339
14. S. L. Schreiber, Science 2000, 287, 1964
15. M. D. Burke, S. L. Schreiber, Angew. Chem. 2004, 116, 48
16. Angew. Chem. Int. Ed. 2004, 43, 46
17. S. L. Schreiber, Nature 2009, 457, 153
18. D. S. Tan, Nat. Chem. Biol. 2005, 1, 74
19. C. Cordier, D. Morton, S. Murrison, A. Nelson, C. O'Leary-Steele, Nat. Prod. Rep. 2008, 25, 719
20. W. R. J. D. Galloway, A. I. Llobet, D. R. Spring, Nat. Commun. 2010, 1, 80
21. S. Oh, S. B. Park, Chem. Commun. 2011, 47, 12754.
22. J. Montgomery, Angew. Chem. 2004, 116, 3980
23. Angew. Chem. Int. Ed. 2004, 43, 3890
24. E. Negishi, C. Coperet, S. Ma, S. Liou, Y. F. Liu, Chem. Rev. 1996, 96, 365
25. L. F. Tietze, Chem. Rev. 1996, 96, 115
26. R. Grigg, V. Sridharan, J. Organomet. Chem. 1999, 576, 65
27. T. Miura, M. Murakami, Chem. Commun. 2007, 217
28. M. Malacria, Chem. Rev. 1996, 96, 289
29. K. C. Nicolaou, T. Montagnon, S. A. Snyder, Chem. Commun. 2003, 551
30. K. C. Nicolaou, D. J. Edmonds, P. G. Bulger, Angew. Chem. 2006, 118, 7292
31. Angew. Chem. Int. Ed. 2006, 45, 7134
32. D. Enders, C. Grondal, M. R. M. Hüttl, Angew. Chem. 2007, 119, 1590
33. Angew. Chem. Int. Ed. 2007, 46, 1570
34. L. F. Tietze, G. Brasche, K. Gericke, Domino Reactions in Organic Synthesis, Wiley-VCH, Weinheim, 2006
35. L. F. Tietze, A. Düfert, F. Lotz, L. Sölter, K. Oum, T. Lenzer, T. Beck, R. Herbst-Irmer, J. Am. Chem. Soc. 2009, 131, 17879
36. L. F. Tietze, M. A. Düfert, T. Hungerland, K. Oum, T. Lenzer, Chem. Eur. J. 2011, 17, 8452
37. J. Panteleev, L. Zhang, M. Lautens, Angew. Chem. 2011, 123, 9255
38. Angew. Chem. Int. Ed. 2011, 50, 9089.
39. X. Chen, P. Lu, Y. Wang, Chem. Eur. J. 2011, 17, 8105
40. Y. Luo, X. Pan, J. Wu, Org. Lett. 2011, 13, 1150
41. Y. Luo, L. Hong, J. Wu, Chem. Commun. 2011, 47, 5298.
42. L.-N. Guo, X.-H. Duan, H.-P. Bi, X.-Y. Liu, Y.-M. Liang, J. Org. Chem. 2006, 71, 3325
43. D. Zhang, Z. Liu, E. K. Yum, R. C. Larock, J. Org. Chem. 2007, 72, 251
44. X.-H. Duan, L.-N. Guo, H.-P. Bi, X.-Y. Liu, Y.-M. Liang, Org. Lett. 2006, 8, 3053
45. L.-N. Guo, X.-H. Duan, X.-Y. Liu, J. Hu, H.-P. Bi, Y.-M. Liang, Org. Lett. 2007, 9, 5425
46. Z. A. Khan, T. Wirth, Org. Lett. 2009, 11, 229
47. Z.-H. Guan, Z.-H. Ren, L.-B. Zhao, Y.-M. Liang, Org. Biomol. Chem. 2008, 6, 1040.