Diaceno[a,e]pentalenes from homoannulations of o-alkynylaryliodides utilizing a unique Pd(OAc)2/n-Bu4NOAc catalytic combination

Organic Letters

Volumn 16, Issue 18, 2014, Pages 4924-4927

  Shen, Junjian ^a,b   Yuan, Dafei ^a   Qiao, Yan ^b   Shen, Xingxing ^a   Zhang, Zhongbo ^a   Zhong, Yuwu ^a   Yi, Yuanping ^a   Zhu, Xiaozhang ^a  

^a INSTITUTE OF CHEMISTRY   (China)

^b INSTITUTE OF COAL CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84918510756     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol502440d     Document Type: Article

References (43)

1. Brand, K. Ber. Dtsch. Chem. Ges. 1912, 45, 3071.
2. Hopf, H. Angew. Chem., Int. Ed. 2013, 52, 12224.
3. (a) Wood, J. D.; Jellison, J. L.; Finke, A. D.; Wang, L.; Plunkett, K. N. J. Am. Chem. Soc. 2012, 134, 15783.
4. (b) Chase, D. T.; Fix, A. G.; Kang, S. J.; Rose, B. D.; Weber, C. D.; Zhong, Y.; Zakharov, L. N.; Lonergan, M. C.; Nuckolls, C.; Haley, M. M. J. Am. Chem. Soc. 2012, 134, 10349.
5. (c) Shimizu, A.; Kishi, R.; Nakano, M.; Shiomi, D.; Sato, K.; Takui, T.; Hisaki, I.; Miyata, M.; Tobe, Y. Angew. Chem., Int. Ed. 2013, 52, 6076 and references cited therein.
6. (a) Saito, M. Symmetry 2010, 2, 950.
7. For selected recent examples, see: (b) London, G.; Von Wantoch Rekowski, M.; Dumele, O.; Schweizer, W. B.; Gisselbrecht, J.-P.; Boudon, C.; Diederich, F. Chem. Sci. 2014, 5, 965.
8. (c) Chen, C.; Harhausen, M.; Liedtke, R.; Bussmann, K.; Fukazawa, A.; Yamaguchi, S.; Petersen, J. L.; Daniliuc, C. G.; Frohlich, R; Kehr, G.; Erker, G. Angew. Chem., Int. Ed. 2013, 52, 5992.
9. (d) Hashmi, A. S. K.; Wieteck, M.; Braun, I.; Nosel, P.; Jongbloed, L.; Rudolph, M.; Rominger, F. Adv. Synth. Catal. 2012, 354, 555.
10. (e) Li, H.; Wei, B.; Xu, L.; Zhang, W.-X.; X, Z. Angew. Chem., Int. Ed. 2013, 52, 10822.
11. Chakraborty, M.; Tessier, C. A.; Youngs, W. J. J. Org. Chem. 1999, 64, 2947.
12. Kawase, T.; Konishi, A.; Hiro, Y.; Matsumoto, K.; Kurata, H.; Kubo, T. Chem.-Eur. J. 2009, 15, 2653.
13. Levi, Z. U.; Tilley, T. D. J. Am. Chem. Soc. 2009, 131, 2796.
14. Maekawa, T.; Segawa, Y.; Itami, K Chem. Sci. 2013, 4, 2369.
15. Zhao, J.; Oniwa, K; Asao, N.; Yamamoto, Y.; Jin, T. J. Am. Chem. Soc. 2013, 135, 10222.
16. Anthony, J. E. Angew. Chem., Int. Ed. 2008, 47, 452.
17. (a) Catellani, M.; Fagnola, M. C. Angew. Chem., Int. Ed. Engl. 1994, 33, 2421.
18. (b) Catellani, M.; Motti, E.; Della Ca, N. Acc. Chem. Res. 2008, 41, 1512.
19. (c) Malacria, M.; Maestri, G. J. Org. Chem. 2013, 78, 1323.
20. (d) Kung, Y.-H.; Cheng, Y.-S.; Tai, C.-C.; Liu, W.-S.; Shin, C.-C.; Ma, C.-C.; Tsai, Y.-C.; Wu, T.-C.; Kuo, M.-Y.; Wu, Y.-T. Chem.-Eur. J. 2010, 16, 5909.
21. (e) Wu, T.-C.; Chen, C.-H.; Hibi, D.; Shimizu, A; Tobe, Y.; Wu, Y.-T. Angew. Chem., Int. Ed. 2010, 49, 7059.
22. (f) Lin, Y.-D.; Cho, C.-L.; Ko, C.-W.; Pulte, A.; Wu, Y.-T. J. Org. Chem. 2012, 77, 9979.
23. Stephenson, T. A.; Morehouse, S. M.; Powell, A. R; Heffer, J. P.; Wilkinson, G J. Chem. Soc. 1965, 3632.
24. (a) Reetz, M. T.; De Vries, J. G Chem. Commun. 2004, 1559.
25. (b) Balanta, A; Godard, C.; Claver, C. Chem. Soc. Rev. 2011, 40, 4973.
26. (c) Deraedt, C.; Astruc, D. Acc. Chem. Res. 2014, 47, 494.
27. (a) Reetz, M. T.; Westermann, E. Angew. Chem., Int. Ed. 2000, 39, 165.
28. (b) Jeffery, T. J. Chem. Soc, Chem, Commun. 1984, 1287.
29. (a) Kawase, T.; Fujiwara, T.; Kitamura, C.; Konishi, A; Hirao, Y.; Matsumoto, K; Kurata, H.; Kubo, T.; Shinamura, S.; Mori, H.; Miyazaki, E.; Takimiya, K Angew. Chem., Int. Ed. 2010, 49, 7728.
30. (b) Nakano, M.; Osaka, I.; Takimiya, K; Koganezawa, T. J. Mater. Chem. C 2014, 2, 64.
31. Maliakal, A.; Raghavachari, K; Katz, H.; Chandross, K; Siegrist, T. Chem. Mater. 2004, 16, 4980.
32. Vicente, J.; Arcas, A; Julia-Hernandez, F.; Bautista, D. Angew. Chem., Int. Ed. 2011, 50, 6896.
33. Whitesides, G M.; Hackett, M.; Brainard, R L.; Lavalleye, J.-P. P. M.; Sowinski, A. F.; Izumi, A. N.; Moore, S. S.; Brown, D. W.; Staudt, E. M. Organometallics 1985, 4, 1819.
34. (a) Li, Y.; Boone, E.; El-Sayed, M. A. Langmuir 2002, 18, 4921.
35. (b) Li, Y.; El-Sayed, M. A. J. Phys. Chem. B 2001, 105, 8938.
36. The pyrolytic transformation from Pd (OAc) 2 to Pd (0) is elusive. (a) Reetz, M. T.; Masse, M. Adv. Mater. 1999, 11, 773.
37. (b) Tano, T.; Esumi, K; Meguro, K J. Colloid Interface Sci. 1989, 133, 530.
38. (c) Gallagher, P. K; Gross, M. E. J. Therm. Anal. 1986, 31, 1231.
39. Ouchi, Y.; Sugiyasu, K; Ogi, S.; Sato, A; Takeuchi, M. Chem. Asian. J. 2012, 7, 75.
40. (a) Falchi, A.; Gellini, C.; Salvi, P. R; Hafner, K J. Phys. Chem. A 1998, 102, 5006.
41. (b) Levi, Z. U.; Tilley, T. D. J. Am. Chem. Soc. 2010, 132, 11012.
42. Zhu, X.; Tsuji, H.; Navarrete, J.; Casado, J.; Nakamura, E. J. Am. Chem. Soc. 2012, 134, 19254.
43. Watanabe, M.; Chang, Y. J.; Liu, S.-W.; Chao, T.-H.; Goto, K; Islam, Md. M.; Yuan, C.-H.; Tao, Y.-T.; Shinmyozu, T.; Chow, T. J. Nat. Chem. 2012, 4, 574.