Rhodium(III)-catalyzed synthesis of cinnolinium salts from azobenzenes and alkynes: Application to the synthesis of indoles and cinnolines

Chemistry - A European Journal

Volumn 19, Issue 20, 2013, Pages 6198-6202

  Muralirajan, Krishnamoorthy ^a   Cheng, Chien Hong ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

air; alkynes; azobenzenes; C H activation; cinnolinium salts; rhodium

Indexed keywords

ALKYNES; C-H ACTIVATION; CATALYZED SYNTHESIS; RHODIUM (III); RHODIUM-CATALYZED SYNTHESIS;

ACTIVATION ANALYSIS; AIR; AZOBENZENE; CATALYSIS; HYDROCARBONS; RHODIUM;

SALTS;

ALKYNE; AZO COMPOUND; AZOBENZENE; CINNOLINE; FUSED HETEROCYCLIC RINGS; INDOLE DERIVATIVE; INORGANIC SALT; RHODIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ALKYNES; AZO COMPOUNDS; CATALYSIS; HETEROCYCLIC COMPOUNDS, 2-RING; INDOLES; MOLECULAR STRUCTURE; RHODIUM; SALTS;

EID: 84877263135     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201300922     Document Type: Article

References (85)

1. W. Kalk, K. H. Schundehutte, US Patent, US4139530, 1979
2. Y. Yu, S. K. Singh, A. Liu, T.-K. Li, L. F. Liub, E. J. LaVoiea, Bioorg. Med. Chem. 2003, 11, 1475
3. S. A. Hitchcock, R. Liu, M. P. Arrington, A. T. Hopper, R. D. Conticello, T. M. Nguyen, M. D. Danca, C. M. Gauss, US Patent, US2007/0265270 A1, 2007
4. W. Lewgowd, A. Stanczak, Arch. Pharm. Chem. Life Sci. 2007, 340, 65
5. B. Hu, R. Unwalla, M. Collini, E. Quinet, I. Feingold, A. G. Nilsson, A. Wihelmsson, P. Nambi, J. Wrobel, Bioorg. Med. Chem. 2009, 17, 3519
6. B. S. Young, J. L. Marshall, E. MacDonald, C. L. Vonnegut, M. M. Haley, Chem. Commun. 2012, 48, 5166.
7. E. C. Kornfeld, J. Am. Chem. Soc. 1948, 70, 1373
8. C. F. H. Allen, J. A. Vanallan, J. Am. Chem. Soc. 1951, 73, 5850
9. C. G. Overberger, R. Sitaramaiah, T. St. Pierre, S. Yaroslavsky, J. Am. Chem. Soc. 1965, 87, 3270
10. H. J. Barber, E. Lunt, K. Washbourn, W. R. Wragg, J. Chem. Soc. C 1967, 1657
11. M. H. Palmer, E. R. R. Russell, J. Chem. Soc. C 1968, 2621
12. D. E. Ames, H. R. Ansari, A. D. G. France, A. C. Lovesey, B. Novitt, R. Simpson, J. Chem. Soc. C 1971, 3088
13. W. Holzer, G. A. Eller, S. Schonberger, Saudi Pharm. J. 2008, 16, 19.
14. G. Wu, A. L. Rhelngold, R. F. Heck, Organometallics 1986, 5, 1922
15. G. Wu, A. L. Rheingold, R. F. Heck, Organometallics 1987, 6, 2386
16. G. Wu, S. J. Geib, A. L. Rheingold, R. F. Heck, J. Org. Chem. 1988, 53, 3238;
17. P. Reiber, Y. Wakatsuki, H. Kisch, Monatsh. Chem. 1995, 126, 1
18. U. R. Aulwurm, J. U. Melchinger, H. Kisch, Organometallics 1995, 14, 3385
19. U. Dürr, F. W. Heinemann, H. Kisch, J. Organomet. Chem. 1997, 541, 307
20. I. D. Jurberg, F. Gagosz, J. Organomet. Chem. 2011, 696, 37.
21. C. J. Ball, J. Gilmore, M. C. Willis, Angew. Chem. Int. Ed. 2012, 51, 5718
22. G. Zhang, J. Miao, Y. Zhao, H. Ge, Angew. Chem. Int. Ed. 2012, 51, 8318.
23. F. Kakiuchi, S. Murai, Acc. Chem. Res. 2002, 35, 826
24. F. Kakiuchi, N. Chatani, Adv. Synth. Catal. 2003, 345, 1077
25. F. Kakiuchi, Top. Organomet. Chem. 2007, 24, 1
26. L. Ackermann, Top. Organomet. Chem. 2007, 24, 35
27. L. Ackermann, R. Vicente, A. Kapdi, Angew. Chem. 2009, 121, 9976
28. Angew. Chem. Int. Ed. 2009, 48, 9792
29. T. Satoh, M. Miura, Chem. Eur. J. 2010, 16, 11212
30. D. A. Colby, R. G. Bergman, J. A. Ellman, Chem. Rev. 2010, 110, 624
31. T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147
32. L. Ackermann, Chem. Rev. 2011, 111, 1315
33. J. F. Hartwig, Chem. Soc. Rev. 2011, 40, 1992
34. J. Wencel-Delord, T. Dröge, F. Liu, F. Glorius, Chem. Soc. Rev. 2011, 40, 4740
35. G. Song, F. Wang, X. Li, Chem. Soc. Rev. 2012, 41, 3651
36. K. M. Engle, T.-S. Mei, M. Wasa, J.-Q. Yu, Acc. Chem. Res. 2012, 45, 788
37. D. A. Colby, A. S. Tsai, R. G. Bergman, J. A. Ellman, Acc. Chem. Res. 2012, 45, 814.
38. N. Chatani, T. Asaumi, T. Ikeda, S. Yorimitsu, Y. Ishii, F. Kakiuchi, S. Murai, J. Am. Chem. Soc. 2000, 122, 12882
39. F. Kakiuchi, S. Kan, K. Igi, N. Chatani, S. Murai, J. Am. Chem. Soc. 2003, 125, 1698
40. F. Kakiuchi, Y. Matsuura, S. Kan, N. Chatani, J. Am. Chem. Soc. 2005, 127, 5936
41. M. V. Pham, B. Ye, N. Cramer, Angew. Chem. Int. Ed. 2012, 51, 10610.
42. N. Umeda, H. Tsurugi, T. Satoh, M. Miura, Angew. Chem. 2008, 120, 4083
43. Angew. Chem. Int. Ed. 2008, 47, 4019
44. Y. Su, M. Zhao, K. Han, G. Song, X. Li, Org. Lett. 2010, 12, 5462
45. A. S. Tsai, M. E. Tauchert, R. G. Bergman, J. A. Ellman, J. Am. Chem. Soc. 2011, 133, 1248
46. S. Rakshit, C. Grohmann, T. Besset, F. Glorius, J. Am. Chem. Soc. 2011, 133, 2350
47. D. R. Stuart, P. Alsabeh, M. Kuhn, K. Fagnou, J. Am. Chem. Soc. 2010, 132, 18326
48. M. Tobisu, H. Kinuta, Y. Kita, E. Rémond, N. Chatani, J. Am. Chem. Soc. 2012, 134, 115
49. B. J. Li, H. Y. Wang, Q. L. Zhu, Z. J. Shi, Angew. Chem. Int. Ed. 2012, 51, 3948
50. J. Ryu, S. H. Cho, S. Chang, Angew. Chem. Int. Ed. 2012, 51, 3677
51. K. Morimoto, M. Itoh, K. Hirano, T. Satoh, Y. Shibata, K. Tanaka, M. Miura, Angew. Chem. Int. Ed. 2012, 51, 5359.
52. N. Guimond, C. Gouliaras, K. Fagnou, J. Am. Chem. Soc. 2010, 132, 6908
53. S. Rakshit, F. W. Patureau, F. Glorius, J. Am. Chem. Soc. 2010, 132, 9585
54. K. Morimoto, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2010, 12, 2068
55. F. Wang, G. Song, X. Li, Org. Lett. 2010, 12, 5430
56. K. D. Hesp, R. G. Bergman, J. A. Ellman, J. Am. Chem. Soc. 2011, 133, 11430
57. S. Duttwyler, C. Lu, A. L. Rheingold, R. G. Bergman, J. A. Ellman, J. Am. Chem. Soc. 2012, 134, 4064
58. H. Wang, F. Glorius, Angew. Chem. Int. Ed. 2012, 51, 7318.
59. L. Li, W. W. Brennessel, W. D. Jones, J. Am. Chem. Soc. 2008, 130, 12414
60. R. P. Korivi, W.-J. Wu, C.-H. Cheng, Chem. Eur. J. 2009, 15, 10727
61. R. P. Korivi, W.-J. Wu, C.-H. Cheng, Chem. Eur. J. 2010, 16, 282
62. W.-C. Shih, C.-C. Teng, K. Parthasarathy, C.-H. Cheng, Chem. Asian J. 2012, 7, 306
63. J. Jayakumar, K. Parthasarathy, C.-H. Cheng, Angew. Chem. Int. Ed. 2012, 51, 197
64. K. Parthasarathy, N. Senthilkumar, J. Jayakumar, C.-H. Cheng, Org. Lett. 2012, 14, 3478.
65. K. Parthasarathy, M. Jeganmohan, C.-H. Cheng, Org. Lett. 2008, 10, 325
66. K. Parthasarathy, C.-H. Cheng, J. Org. Chem. 2009, 74, 9359
67. V. S. Thirunavukkarasu, K. Parthasarathy, C.-H. Cheng, Angew. Chem. 2008, 120, 9604
68. Angew. Chem. Int. Ed. 2008, 47, 9462
69. V. S. Thirunavukkarasu, K. Parthasarathy, C.-H. Cheng, Chem. Eur. J. 2010, 16, 1436
70. P. Gandeepan, K. Parthasarathy, C.-H. Cheng, J. Am. Chem. Soc. 2010, 132, 8569
71. K. Muralirajan, K. Parthasarathy, C.-H. Cheng, Angew. Chem. 2011, 123, 4255
72. Angew. Chem. Int. Ed. 2011, 50, 4169
73. J. Karthikeyan, C.-H. Cheng, Angew. Chem. 2011, 123, 10054
74. Angew. Chem. Int. Ed. 2011, 50, 9880
75. P. Gandeepan, C.-H. Cheng, J. Am. Chem. Soc. 2012, 134, 5738
76. K. Muralirajan, K. Parthasarathy, C.-H. Cheng, Org. Lett. 2012, 14, 4262
77. J. Karthikeyan, R. Haridharan, C.-H. Cheng, Angew. Chem. Int. Ed. 2012, 51, 12343.
78. Y. M. Wu, L. Y. Ho, C.-H. Cheng, J. Org. Chem. 1985, 50, 392.
79. D. K. Rayabarapu, C. H. Yang, C.-H. Cheng, J. Org. Chem. 2003, 68, 6726
80. K. J. Chang, D. K. Rayabarapu, C.-H. Cheng, Org. Lett. 2003, 5, 3963
81. M. Ohtaka, H. Nakamura, Y. Yamamoto, Tetrahedron Lett. 2004, 45, 7339
82. R. P. Korivi, C.-H. Cheng, Org. Lett. 2005, 7, 5179.
83. S. D. Koulocheri, S. A. Haroutounian, Eur. J. Org. Chem. 2001, 1723
84. US Patent, US 2003/0220377 A1, 2003.
85. CCDC-907964 (5 a), CCDC-907965 (1 b-I), CCDC-907966 (3 w), and CCDC-907967 (3 t) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.