Pd-catalyzed cascade crossover annulation of o-alkynylarylhalides and diarylacetylenes leading to dibenzo[a,e]pentalenes

Journal of the American Chemical Society

Volumn 135, Issue 28, 2013, Pages 10222-10225

  Zhao, Jian ^a   Oniwa, Kazuaki ^a   Asao, Naoki ^a   Yamamoto, Yoshinori ^a,b   Jin, Tienan ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b DALIAN UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC RINGS; ARYLACETYLENES; C-H ACTIVATION; DIARYLACETYLENES; HIGH YIELD; OPTIMIZED REACTION CONDITIONS; PENTALENES;

ACTIVATION ANALYSIS; FUNCTIONAL GROUPS;

CATALYSIS;

2 ALKYNYLARYLHALIDE; ACETYLENE DERIVATIVE; ALKYNE; AROMATIC COMPOUND; CARBON; DIARYLACETYLENE; DIBENZO[ A,E ]PENTALENE; DIBENZOPENTALENE; HALIDE; HYDROGEN; PALLADIUM COMPLEX; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CARBOPALLADATION; CATALYSIS; CONTROLLED STUDY; CROSS COUPLING REACTION; CRYSTAL STRUCTURE; RING OPENING; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALKYNES; CATALYSIS; CYCLOPENTANES; HYDROCARBONS, HALOGENATED; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM;

EID: 84880391045     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja403382d     Document Type: Article

References (42)

1. Levi, Z. U.; Tilley, T. D. J. Am. Chem. Soc. 2010, 132, 11012
2. Chase, D. T.; Rose, B. D.; McClintock, S. P.; Zakharov, L. N.; Haley, M. M. Angew. Chem., Int. Ed. 2011, 50, 1127
3. Chase, D. T.; Fix, A. G.; Rose, B. D.; Weber, C. D.; Nobusue, S.; Stockwell, C. E.; Zakharov, L. N.; Lonergan, M. C.; Haley, M. M. Angew. Chem., Int. Ed. 2011, 50, 11103
4. Shimizu, A.; Tobe, Y. Angew. Chem., Int. Ed. 2011, 50, 6906
5. 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
6. Nishida, J.; Tsukaguchi, S.; Yamashita, Y. Chem.-Eur. J. 2012, 18, 8964
7. 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
8. Zhu, X.; Mitsui, C.; Tsuji, H.; Nakamura, E. J. Am. Chem. Soc. 2009, 131, 13596
9. Anthony, J. E. Chem. Rev. 2006, 106, 5028
10. Anthony, J. E. Angew. Chem., Int. Ed. 2008, 47, 452
11. Saito, M.; Nakamura, T.; Tajima, T. Chem.-Eur. J. 2008, 14, 6062
12. Kawase, T.; Konishi, A.; Hirao, Y.; Matsumoto, K.; Kurata, H.; Kubo, T. Chem.-Eur. J. 2009, 15, 2653
13. Zhang, H.; Karasawa, T.; Yamada, H.; Wakamiya, A.; Yamaguchi, S. Org. Lett. 2009, 11, 3076
14. Saito, M. Symmetry 2010, 2, 950
15. Brand, K. Ber. Detsch. Chem. Ges. 1912, 45, 3071
16. Ballester, M.; Castaner, J.; Riera, J.; Armet, O. J. Org. Chem. 1986, 51, 1100
17. Blum, J.; Baidossi, W.; Badrieh, Y.; Hoffmann, R. E.; Schumann, H. J. Org. Chem. 1995, 60, 4738
18. Chakraborty, M.; Tessier, C. A.; Youngs, W. J. J. Org. Chem. 1999, 64, 2947
19. Saito, M.; Nakamura, M.; Tajima, T.; Yoshioka, M. Angew. Chem., Int. Ed. 2007, 46, 1504
20. Babu, G.; Orita, A.; Otera, J. Chem. Lett. 2008, 37, 1296
21. Levi, Z. U.; Tilley, T. D. J. Am. Chem. Soc. 2009, 131, 2796
22. Wu, T.-C.; Tai, C.-C.; Tiao, H.-C.; Kuo, M.-Y.; Wu, Y.-T. Chem.-Eur. J. 2011, 17, 1930
23. Hashmi, A. S. K.; Wieteck, M.; Braun, I.; Nösel, P.; Jongbloed, L.; Rudolph, M.; Rominger, F. Adv. Synth. Catal. 2012, 354, 555
24. Xu, F.; Peng, L.; Orita, A.; Otera, J. Org. Lett. 2012, 14, 3970
25. Maekawa, T.; Segawa, Y.; Itami, K. Chem. Sci. 2013, 4, 2369
26. Yang, J.; Lakshmikantham, M. V.; Cava, M. P. J. Org. Chem. 2000, 65, 6739
27. Jeffrey, J. L.; Sarpong, R. Tetrahedron Lett. 2009, 50, 1969
28. Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111, 1780
29. Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215
30. Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem., Int. Ed. 2012, 51, 8960
31. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
32. Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094
33. Lafrance, M.; Gorelsky, S. I.; Fagnou, K. J. Am. Chem. Soc. 2007, 129, 14570
34. Rousseaux, S.; Gorelsky, S. I.; Chung, B. K. W.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 10692
35. Ackermann, L. Chem. Rev. 2011, 111, 1315
36. Lapointe, D.; Fagnou, K. Chem. Lett. 2010, 39, 1118
37. CCDC 932167 contains the supplementary crystallography data of 3e. This data can be download free of charge via www.ccdc.cam.ac.uk/conts/retrieving. html.
38. Takimiya, K.; Ebata, H.; Sakamoto, K.; Izawa, T.; Otsubo, T.; Kunugi, Y. J. Am. Chem. Soc. 2006, 128, 12604
39. Tang, M. L.; Okamoto, T.; Bao, Z. J. Am. Chem. Soc. 2006, 128, 16002
40. Tonzola, C. J.; Alam, M. M.; Kaminsky, W.; Jenekhe, S. A. J. Am. Chem. Soc. 2003, 125, 13548
41. Negishi, E.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. J. Am. Chem. Soc. 1996, 96, 365
42. Quan, L. G.; Gevorgyan, Y.; Yamamoto, Y. J. Am. Chem. Soc. 1999, 121, 3545