Synthesis of α,ω -diarylbutadienes and -hexatrienes via decarboxylative coupling of cinnamic acids with vinyl bromides under palladium catalysis

Organic Letters

Volumn 12, Issue 3, 2010, Pages 592-595

  Yamashita, Mana ^a   Hirano, Koji ^a   Satoh, Tetsuya ^a   Miura, Masahiro ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 75749132759     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9027896     Document Type: Article

References (62)

1. Selected reviews: (a) Barnard, J. H.; Collings, J. C.; Whiting, A.; Przyborski, S. A.; Marder, T. B. Chem.-Eur. J. 2009, 15, 11430.
2. (b) Thirsk, C.; Whiting, A. J. Chem. Soc., Perkin Trans. 1 2002, 999.
3. Rychnovsky, S. D.; Rogers, B. N.; Richardson, T. I. Acc Chem. Res. 1998, 31, 9.
4. Rychnovsky, S. D. Chem. Rev. 1995, 95, 2021.
5. For recent example, see: (a) Shimizu, M.; Tatsumi, H.; Mochida, K.; Shimono, K.; Hiyama, T. Chem. Asian J. 2009, 4, 1289.
6. (b) Lawrentz, U.; Grahn, W.; Lukaszuk, K.; Klein, C.; Wortmann, R.; Feldner, A.; Scherer, D. Chem-Eur. J. 2002, 8, 1573.
7. (c) Suzuki, T.; Higuchi, H.; Ohkita, M.; Tsuji, T. Chem. Commun. 2001, 1574.
8. (d) Kim, J.-H.; Noh, S.; Kim, K.; Lim, S.-T.; Shin, D.-M. Synth. Met. 2001, 117, 111.
9. (e) Hünig, S.; Kemmer, M.; Wenner, H.; Barbosa, F.; Gescheidt, G.; Perepichka, I. F.; Bäuerle, P.; Emge, A.; Peters, K. Chem.-Eur. J. 2000, 6, 2618.
10. (a) Davis, R.; Kumar, N. S. S.; Abraham, S.; Suresh, C. H.; Rath, N. P.; Tamaoki, N.; Das, S. J. Phys. Chem. C 2008, 112, 2137.
11. (b) Sonoda, Y.; Goto, M.; Tsuzuki, S.; Tamaoki, N. J. Phys. Chem. A 2007, 111, 13441.
12. (c) Sonoda, Y.; Goto, M.; Tsuzuki, S.; Tamaoki, N. J. Phys. Chem. A 2006, 110, 13379.
13. (d) Abraham, S.; Mallia, V. A.; Ratheesh, V.; Tamaoki, N.; Das, S. J. Am. Chem. Soc. 2006, 128, 7692.
14. (e) Lightfoot, A. P.; Twiddle, S. J. R.; Whiting, A. Org. Biomol. Chem. 2005, 3, 3167.
15. (f) Denmark, S. E.; Tymonko, S. A. J. Am. Chem. Soc. 2005, 127, 8004.
16. (g) Davis, R.; Mallia, V. A.; Das, S.; Tamaoki, N. Adv. Funct. Mater. 2004, 14, 743.
17. (h) Davis, R.; Abraham, S.; Rath, N. P.; Das, S. New J. Chem. 2004, 28, 1368.
18. (i) Sonoda, Y.; Kawanishi, Y.; Ikeda, T.; Goto, M.; Hayashi, S.; Yoshida, Y.; Tanigaki, N.; Yase, K. J. Phys. Chem. B 2003, 107, 3376.
19. (j) Davis, R.; Mallia, V. A.; Das, S. Chem. Mater. 2003, 15, 1057.
20. (k) Bartkowiak, W.; Zalesny, R.; Niewodniczanski, W.; Leszczynski, J. J. Phys. Chem. A 2001, 105, 10702.
21. (l) Locknar, S. A.; Peteanu, L. A.; Shuai, Z. J. Phys. Chem. A 1999, 103, 2197.
22. (m) Andraud, C.; Zabulón, T.; Collet, A.; Zyss, J. Chem. Phys. 1999, 245, 243.
23. (n) Crousse, B.; Alami, M.; Linstrumelle, G. Tetrahedron Lett. 1997, 38, 5297.
24. (o) Cheng, L.-T.; Tarn, W.; Marder, S. R.; Stiegman, A. E.; Rikken, G.; Spangler, C. W. J. Phys. Chem. 1991, 95, 10643.
25. (p) Allen, M. T.; Whitten, D. G. Chem. Rev. 1989, 89, 1691.
26. Selected reviews: (a) Negishi, E.-I.; Huang, Z.; Wang, G.; Mohan, S.; Wang, C.; Hattori, H. Acc Chem. Res. 2008, 41, 1474.
27. (b) Satoh, T.; Tsurugi, H.; Miura, M. Chem. Rec 2008, 8, 326.
28. (c) Vasil'ev, A. A.; Serebryakov, E. P. Russ. Chem. Rev. 2001, 70, 735.
29. Selected reviews: (a) Goossen, L. J.; Rodriguez, N.; Goossen, K. Angew. Chem., Int. Ed. 2008, 47, 3100.
30. (b) Baudoin, O. Angew. Chem., Int. Ed. 2007, 46, 1373. For reviews concerning coupling via C-C bond cleavage, see:
31. (c) Yorimitsu, H.; Oshima, K. Bull. Chem. Soc. Jpn. 2009, 82, 778.
32. (d) Park, Y. J.; Park, J.-W.; Jun, C.-H. Acc. Chem. Res. 2008, 41, 111.
33. (e) Catellani, M.; Motti, E.; Delia Ca', N. Acc. Chem. Res. 2008, 41, 1512.
34. (f) Nakao, Y.; Hiyama, T. Pure Appl. Chem. 2008, 80, 1097.
35. (g) Tobisu, M.; Chatani, N. Chem. Soc. Rev. 2008, 37, 300.
36. (h) Satoh, T.; Miura, M. Top Organomet. Chem. 2007, 24, 61.
37. (i) Murakami, M.; Makino, M.; Ashida, S.; Matsuda, T. Bull. Chem. Soc. Jpn. 2006, 79, 1315.
38. (j) Kondo, T.; Mitsudo, T. Chem. Lett. 2005, 34, 1462.
39. (k) Jun, C.-H. Chem. Soc. Rev. 2004, 33, 610.
40. (l) Nishimura, T.; Uemura, S. Synlett 2004, 201.
41. (m) van der Boom, M. E.; Milstein, D. Chem. Rev. 2003, 103, 1759.
42. (n) Perthuisot, C.; Edelbach, B. L.; Zubris, D. L.; Simhai, N.; Iverson, C. N.; Müller, C.; Satoh, T.; Jones, W. D. J. Mol. Catal. A: Chem. 2002, 189, 157.
43. (a) Yamashita, M.; Horiguchi, H.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2009, 74, 7481.
44. (b) Shimizu, M.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2009, 74, 3478.
45. (c) Miyasaka, M.; Hirano, K.; Satoh, T.; Miura, M. Adv. Synth. Catal. 2009, 351, 2683.
46. (d) Yamashita, M.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2009, 11, 2337.
47. (e) Miyasaka, M.; Fukushima, A.; Satoh, T.; Hirano, K.; Miura, M. Chem.-Eur. J. 2009, 15, 3674.
48. (f) Maehara, A.; Tsurugi, H.; Satoh, T.; Miura, M. Org. Lett. 2008, 10, 1159.
49. (g) Nakano, M.; Tsurugi, H.; Satoh, T.; Miura, M. Org. Lett. 2008, 10, 1851.
50. (h) Ueura, K.; Satoh, T.; Miura, M. J. Org. Chem. 2007, 72, 5362.
51. (a) Tsujiyama, S.; Ueno, M. Biosci. Biotechnol. Biochem. 2008, 72, 111.
52. (b) Nomura, E.; Hosoda, A.; Mori, H.; Taniguchi, H. Green Chem. 2005, 7, 863.
53. Nomura, E.; Kashiwada, A.; Hosoda, A.; Nakamura, K.; Morishita, H.; Tsuno, T.; Taniguchi, H. Bioorg. Med. Chem. 2003, 11, 3807.
54. (a) Das, J. P.; Roy, S. J. Org. Chem. 2002, 67, 7861.
55. (b) Kuang, C.; Yang, Q.; Senboku, H.; Tokuda, M. Synlett 2000, 1439.
56. Naskar, D.; Roy, S. Tetrahedron 2000, 56, 1369.
57. Chowdhury, S.; Roy, S. J. Org. Chem. 1997, 62, 199.
58. (a) Amatore, C.; Jutand, A.; Suarez, A. J. Am. Chem. Soc. 1993, 115, 9531.
59. (b) Amatore, C.; Azzabi, M.; Jutand, A. J. Am. Chem. Soc. 1991, 113, 8375.
60. (a) Lu, P.; Sanchez, C.; Cornelia, J.; Larrosa, I. Org. Lett. 2009, 11, 5710.
61. (b) Goossen, L. J.; Linder, C.; Rodriguez, N.; Lange, P. P.; Fromm, A. Chem. Commun. 2009, 7173.
62. Cornelia, J.; Sanchez, C.; Banawa, D.; Larrosa, I. Chem. Commun. 2009, 7176.