Hypervalent iodine induced oxidative cross coupling Via thiophene cation radical intermediate

Heterocycles

Volumn 86, Issue 1, 2012, Pages 767-776

  Dohi, Toshifumi ^a   Ito, Motoki ^a   Sekiguchi, Sho ^a   Ishikado, Yohei ^a   Kita, Yasuyuki ^a  

^a RITSUMEIKAN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84880574301     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/COM-12-S(N)39     Document Type: Article

References (50)

1. E. Negishi, Angew. Chem. Int. Ed. (Nobel Lecture), 2011, 50, 6738;
2. A. Suzuki, Angew. Chem. Int. Ed. (Nobel Lecture), 2011, 50, 6722;
3. Metal-Catalyzed Cross-Coupling Reactions, F. Diederich, P. J. Stang Eds.; Wiley-VCH: New York, 2004.
4. R. Noyori, Chem. Soc. Rev., 1989, 18, 187;
5. K. Narasaka, Synthesis, 1991, 1;
6. G. Bringmann, R. Walter, and R. Weirich, Angew. Chem., Int. Ed. Engl., 1990, 29, 977;
7. G. M. Keserú and M. Nógrádi, In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1998; Vol. 20, pp 263;
8. I. Cepanec, Synthesis of Biaryls, Elsevier: New York, 2004.
9. G. P. McGlacken and L. M. Bateman, Chem. Soc. Rev., 2009, 38, 2447;
10. J. A. Ashenhurst, Chem. Soc. Rev., 2010, 39, 540;
11. C. S. Yeung and V. M. Dong, Chem. Rev., 2011, 111, 1215.
12. D. R. Stuart and K. Fagnou, Science, 2007, 316, 1172;
13. D. R. Stuart, E. Villemure, and K. Fagnou, J. Am. Chem. Soc., 2007, 129, 12072;
14. T. A. Dwight, N. R. Rue, D. Charyk, R. Josselyn, and B. DeBoef, Org. Lett., 2007, 9, 3137;
15. S. H. Cho, S. J. Hwang, and S. Chang, J. Am. Chem. Soc., 2008, 130, 9254;
16. P. Xi, F. Yang, S. Qin, D. Zhao, J. Lan, G. Gao, C. Hu, and J. You, J. Am. Chem. Soc., 2010, 132, 1822;
17. C.-Y. He, S. Fan, and X. Zhang, J. Am. Chem. Soc., 2010, 132, 12850;
18. Z. Wang, K. Li, D. Zhao, J. Lan, and J. You, Angew. Chem. Int. Ed., 2011, 50, 5365.
19. Y. Kita, T. Dohi, and K. Morimoto, J. Synth. Org. Chem. Jpn., 2011, 69, 1241;
20. Y. Kita, T. Dohi, and K. Morimoto, Kagaku, 2011, 66, 12;
21. Y. Kita and T. Dohi, Fain Kemikaru, 2011, 40, 49;
22. Y. Kita and T. Dohi, Shokubai, 2012, 54, 145.
23. Y. Kita, H. Tohma, K. Hatanaka, T. Takada, S. Fujita, S. Mitoh, H. Sakurai, and S. Oka, J. Am. Chem. Soc., 1994, 116, 3684;
24. Y. Kita, T. Takada, and H. Tohma, Pure Appl. Chem., 1996, 68, 627;
25. T. Dohi, M. Ito, N. Yamaoka, K. Morimoto, H. Fujioka, and Y. Kita, Tetrahedron, 2009, 65, 10797.
26. T. Wirth, M. Ochiai, V. V. Zhdankin, G. F. Koser, H. Tohma, and Y. Kita, in Top. Curr. Chem.: Hypervalent Iodine Chemistry Modern Developments in Organic Synthesis, T. Wirth (ed.), Springer-Verlag, Berlin (2003);
27. V. V. Zhdankin and P. J. Stang, Chem. Rev., 2008, 108, 5299;
28. T. Dohi and Y. Kita, Chem. Commun., 2009, 2073;
29. L. F. Silva, Jr. and B. Olofsson, Nat. Prod. Rep., 2011, 28, 1722;
30. V. V. Zhdankin, J. Org. Chem., 2011, 76, 1185.
31. Y. Kita, M. Gyoten, M. Ohtsubo, H. Tohma, and T. Takada, Chem. Commun., 1996, 1481;
32. T. Takada, M. Arisawa, M. Gyoten, R. Hamada, H. Tohma, and Y. Kita, J. Org. Chem., 1998, 63, 7698;
33. H. Tohma, H. Morioka, S. Takizawa, M. Arisawa, and Y. Kita, Tetrahedron, 2001, 57, 345;
34. H. Tohma, M. Iwata, T. Maegawa, and Y. Kita, Chem. Eur. J., 2002, 8, 5377.
35. T. Dohi, M. Ito, K. Morimoto, M. Iwata, and Y. Kita, Angew. Chem. Int. Ed., 2008, 47, 1301;
36. T. Dohi, M. Ito, I. Itani, N. Yamaoka, K. Morimoto, H. Fujioka, and Y. Kita, Org. Lett., 2011, 13, 6208.
37. H. Mayr and A. R. Ofial, Angew. Chem., Int. Ed. Engl., 1992, 31, 1613;
38. H. Mayr and M. Patz, Angew. Chem., Int. Ed. Engl., 1994, 33, 938.
39. Y. Kita, K. Morimoto, M. Ito, C. Ogawa, A. Goto, and T. Dohi, J. Am. Chem. Soc., 2009, 131, 1668;
40. T. Dohi, M. Ito, N. Yamaoka, K. Morimoto, H. Fujioka, and Y. Kita, Angew. Chem., Int. Ed., 2010, 49, 3334;
41. K. Morimoto, N. Yamaoka, C. Ogawa, T. Nakae, H. Fujioka, T. Dohi, and Y. Kita, Org. Lett., 2010, 12, 3804.
42. K. Morimoto, T. Nakae, N. Yamaoka, T. Dohi, and Y. Kita, Eur. J. Org. Chem., 2011, 6326.
43. H. Tohma, M. Iwata, T. Maegawa, Y. Kiyono, A. Maruyama, and Y. Kita, Org. Biomol. Chem., 2003, 1, 1647;
44. T. Dohi, K. Morimoto, Y. Kiyono, A. Maruyama, H. Tohma, and Y. Kita, Chem. Commun., 2005, 2930.
45. A. Rahimi, J. C. Namyslo, M. H. H. Drafz, J. Halm, E. Huebner, M. Nieger, N. Rautzenberg, and A. Schmidt, J. Org. Chem., 2011, 76, 7316
46. R. M. S. Maior, K. Hinkelmann, H. Eckert, and F. Wudl, Macromolecules, 1990, 23, 1268;
47. M. Takahashi, K. Masui, H. Sekiguchi, N. Kobayashi, A. Mori, M. Funahashi, and N. Tamaoki, J. Am. Chem. Soc., 2006, 128, 10930.
48. P. Amaladass, J. A. Clement, and A. K. Mohanakrishnan, Tetrahedron, 2007, 63, 10363 and references therein;
49. A. G. Geldhof, and L. Antoine, Tetrahedron Lett., 2006, 47, 9249.
50. B. F. Crowe and F. F. Nord, J. Org. Chem., 1950, 15, 1177.