Iron-catalyzed oxidative homo-coupling of indoles via C-H cleavage

Tetrahedron Letters

Volumn 51, Issue 52, 2010, Pages 6847-6851

  Niu, Tianmin ^a   Zhang, Yuhong ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

3,3 Biindolyl; C H activation; Homo coupling; Iron catalyst

Indexed keywords

2 ARYLINDOLE; 2 PHENYLINDOLE DERIVATIVE; 2,3 DICHLORO 5,6 BISCYANOBENZOQUINONE; 3,3' BIINDOLYL; BENZOQUINONE DERIVATIVE; CARBON; FERRIC CHLORIDE; HYDROGEN; INDOLE DERIVATIVE; IRON; OXYGEN; TETRACHLOROHYDROQUINONE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CROSS COUPLING REACTION; DIMERIZATION; DRUG STRUCTURE; ELECTRON TRANSPORT; OXIDATION KINETICS; SINGLE ELECTRON TRANSFER; STOICHIOMETRY;

EID: 78650677401     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.10.088     Document Type: Article

References (79)

1. (a) Gribble, G. W.; Berthel, S. J. In Studies in Natural Products Chemistry; Attaur-Rahman, Ed.; Elsevier: New York, 1993; Vol. 12, p 365;
2. (b) Pindur, U.; Kim, Y. S.; Mehrabani, F. Curr. Med. Chem. 1999, 6, 29;
3. (c) Ito, S. Pigment Cell Res. 2003, 16, 230;
4. (d) Lather, V.; Kristam, R.; Saini, J. S.; Kristam, R.; Karthikeyan, N. A.; Balaji, V. N. QSAR Comb. Sci. 2008, 27, 718;
5. (e) Janosik, T.; Bergman, Jan.; Stensland, B.; Stalhandske, C. J. Chem. Soc., Perkin Trans. 1 2002, 330;
6. (f) Pezzella, A.; Panzella, L.; Natangelo, A.; Arzillo, M.; Napolitano, A.; Ischia, M. J. Org. Chem. 2007, 72, 9225;
7. (g) Berens, U.; Brown, J. M.; Long, J.; Selke, R. Tetrahedron: Asymmetry 1996, 7, 285;
8. (h) Leclerc, S.; Garnier, M.; Hoessel, R.; Marko, D.; Bibb, J. A.; Snyder, G. L.; Greengard, P.; Biernati, J.; Wui, Y.; Mandelkowi, E.; Eisenbrand, G.; Meijer, L. J. Biol. Chem. 2001, 276, 251.
9. (a) Greci, L.; Tommasi, G.; Astolfi, P.; Petrucci, R.; Marrosu, G.; Trazza, A.; Sgarabotto, P.; Righi, L. J. Chem. Soc., Perkin Trans. 2 2000, 1749;
10. (b) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Parisi, L. M. J. Org. Chem. 2005, 70, 6213;
11. (c) Cacchi, S.; Fabrizi, G.; Lamba, D.; Marinelli, F.; Parisi, L. M. Synthesis 2003, 728;
12. (d) Cardillo, B.; Conti, C.; Ciorgini, E.; Greci, L.; Stipa, P.; Tosi, G. J. Heterocycl. Chem. 1992, 29, 1349;
13. (e) Balogh-Hergovich, E.; Speier, G. J. Chem. Soc., Perkin Trans. 1 1986, 2305;
14. (f) Sundberg, R. J.J. Org. Chem. 1965, 30, 3604;
15. (g) Bruni, P.; Conti, C.; Tosi, G. Monatsh. Chem. 1998, 119, 1311.
16. Desarbre, E.; Bergman, J. J. Chem. Soc., Perkin Trans. 1 1998, 2009.
17. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457;
18. (b) Suzuki, A. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998; pp 49-97. Chapter 2;
19. (c) Liu, L.; Zhang, Y.; Wang, Y. J. Org. Chem. 2005, 70, 6122;
20. (d) Wang, L.; Zhang, Y.; Liu, L.; Wang, Y. J. Org. Chem. 2006, 71, 1284;
21. (e) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 75, 508;
22. (f) Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; pp 167-202;
23. (g) Negishi, E. I. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; pp 1-48. Chapter 1;
24. (h) Huang, J.; Nolan, S. P.J. Am. Chem. Soc. 1999, 121, 9889;
25. (i) Frid, M.; Pèrez, D.; Peat, A. J.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9469.
26. Merlic, C. A.; You, Y.; Mclnnes, D. M.; Zechman, A. L.; Miller, M. M.; Deng, Q. Tetrahedron 2001, 57, 5199.
27. Duong, H. A.; Chua, S.; Huleatt, P. B.; Chai, C. L. L. J. Org. Chem. 2008, 73, 9177.
28. (a) Stuart, D. R.; Fagnou, K. Science 2007, 316, 1172;
29. (b) Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2007, 129, 11904;
30. (c) Seregin, I. V.; Ryabova, V.; Gevorgyan, V. J. Am. Chem. Soc. 2007, 129, 7742;
31. (d) Lewis, J. C.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2008, 41, 1013;
32. (e) Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826;
33. (f) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174;
34. (g) Roy, A. H.; Lenges, C. P.; Brookhart, M. J. Am. Chem. Soc. 2007, 129, 2082;
35. (h) Labinger, J. A.; Bercaw, J. E. Nature 2002, 417, 507;
36. (i) Lersch, M.; Tilset, M. Chem. Rev. 2005, 105, 2471;
37. (j) Zhao, L.; Li, C.-J. Angew. Chem., Int. Ed. 2008, 47, 7075;
38. (k) Shi, B.-F.; Maugel, N.; Zhang, Y.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2008, 47, 4882;
39. (l) Nakao, Y.; Kanyiva, K. S.; Hiyama, T. J. Am. Chem. Soc. 2008, 130, 2448;
40. (m) Campeau, L. C.; Parisien, M.; Leblanc, M.; Fagnou, K. J. Am. Chem. Soc. 2004, 126, 9186;
41. (n) Do, H.-Q.; Daugulis, O. J. Am. Chem. Soc. 2007, 129, 12404;
42. (o) Ruan, J.; Saidi, O.; Iggo, J. A.; Xiao, J. J. Am. Chem. Soc. 2008, 130, 10510;
43. (p) Brasche, G.; García-Fortanet, J.; Buchwald, S. L. Org. Lett. 2008, 10, 2207;
44. (q) Do, H.-Q.; Daugulis, O. J. Am. Chem. Soc. 2009, 131, 17052;
45. (r) Truong, T.; Alvarado, J.; Tran, L. D.; Daugulis, O. Org. Lett. 2010, 12, 1200.
46. Li, Y.; Wang, W.-H.; Yang, S.-D.; Li, B.-J.; Feng, C.; Shi, Z.-J. Chem. Commun. 2010, 46, 4553.
47. Liang, Z.; Zhao, J.; Zhang, Y. J. Org. Chem. 2010, 75, 170.
48. (a) Bolm, C.; Legros, J.; Paih, J. L.; Zani, L. Chem. Rev. 2004, 104, 6217;
49. (b) Bonnamour, J.; Bolm, C. Org. Lett. 2008, 10, 2665;
50. (c) Correa, A.; Carril, M.; Bolm, C. Angew. Chem., Int. Ed. 2008, 47, 2880;
51. (d) Fürstner, A.; Leitner, A.; Méndez, M.; Krause, H. J. Am. Chem. Soc. 2002, 124, 13856;
52. (e) Plietker, B. Angew. Chem., Int. Ed. 2006, 45, 6053;
53. (f) Kofink, C. C.; Blank, B.; Pagano, S.; Gotz, N.; Knochel, P. Chem. Commun. 2007, 1954.
54. (a) Carril, M.; Correa, A.; Bolm, C. Angew. Chem., Int. Ed. 2008, 47, 4862;
55. (b) Hatakeyama, T.; Hashimoto, S.; Ishizuka, K.; Nakamura, M. J. Am. Chem. Soc. 2009, 131, 11949;
56. (c) Czaplik, W. M.; Mayer, M.; Wangelin, A. J. Angew. Chem., Int. Ed. 2009, 48, 607;
57. (d) Hatakeyama, T.; Yoshimoto, Y.; Gabriel, T.; Nakamura, M. Org. Lett. 2008, 10, 5341;
58. (e) Volla, C. M. R.; Vogel, P. Angew. Chem., Int. Ed. 2008, 47, 1305;
59. (f) Hatakeyama, T.; Nakamura, M. J. Am. Chem. Soc. 2007, 129, 9844;
60. (g) Nagano, T.; Hayashi, T. Org. Lett. 2005, 7, 491;
61. (h) Yoshikai, N.; Matsumoto, A.; Norinder, J.; Nakamura, E. Angew. Chem., Int. Ed. 2009, 48, 2925.
62. (a) Yao, B.; Liang, Z.; Niu, T.; Zhang, Y. J. Org. Chem. 2009, 74, 4630;
63. (b) Correa, A.; Bolm, C. Angew. Chem., Int. Ed. 2007, 46, 8862;
64. (c) Guo, D.; Huang, H.; Xu, J.; Jiang, H.; Liu, H. Org. Lett. 2008, 10, 4513.
65. (a) Li, Z.; Cao, L.; Li, C.J. Angew. Chem., Int. Ed. 2007, 119, 6625;
66. (b) Li, Z.; Yu, R.; Li, H. Angew. Chem., Int. Ed. 2008, 47, 7497;
67. (c) Zhang, Y.; Li, C.-J. Eur. J. Org. Chem. 2007, 4654;
68. (d) Li, H.; He, Z.; Guo, X.; Li, W.; Zhao, X.; Li, Z. Org. Lett. 2009, 11, 4176;
69. (e) Pan, S.; Liu, J.; Li, H.; Wang, Z.; Guo, X.; Li, Z. Org. Lett. 2010, 12, 1932;
70. (f) Li, Y.-Z.; Li, B.-J.; Lu, X.-Y.; Lin, S.; Shi, Z.-J. Angew. Chem., Int. Ed. 2009, 48, 3817;
71. (g) Wen, J.; Zhang, J.; Chen, S.-Y.; Li, J.; Yu, X.-Q. Angew. Chem., Int. Ed. 2008, 47, 8897.
72. (a) Huang, L.; Zhang, X.; Zhang, Y. Org. Lett. 2009, 11, 3730;
73. (b) Cheng, K.; Huang, L.; Zhang, Y. Org. Lett. 2009, 11, 2908;
74. (c) Liang, Z.; Yao, B.; Zhang, Y. Org. Lett. 2010, 12, 3185;
75. (d) Zhao, J.; Zhang, Y.; Cheng, K. J. Org. Chem. 2008, 73, 7428.
76. (a) Murata, M.; Miura, M.; Nomura, M. Chem. Commun. 1989, 116;
77. (b) Skiles, G. L.; Yost, G. S. Chem. Res. Toxicol. 1996, 9, 291;
78. (c) Dohi, T.; Ito, M.; Morimoto, K.; Iwata, M.; Kita, Y. Angew. Chem., Int. Ed. 2008, 47, 1301.
79. 6) δ 137.0, 135.1, 133.4, 129.9, 128.8, 127.3, 126.8, 122.3, 119.8, 119.6111.8 106.8.