Synthesis of phenanthridinones from N-methoxybenzamides and aryltriethoxysilanes through RhIII-catalyzed C-H and N-H bond activation

Chemistry - An Asian Journal

Volumn 8, Issue 9, 2013, Pages 2175-2181

  Senthilkumar, Natarajan ^a   Parthasarathy, Kanniyappan ^a   Gandeepan, Parthasarathy ^a   Cheng, Chien Hong ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

annulation; C H activation; phenanthridinones; rhodium; synthetic methods

Indexed keywords

ANNULATION; ANNULATION REACTIONS; C-H ACTIVATION; CATALYTIC REACTIONS; CH-BOND ACTIVATION; N-H BOND ACTIVATION; PHENANTHRIDINONES; SYNTHETIC METHODS;

ACTIVATION ANALYSIS; CATALYSIS; ISOTOPES;

RHODIUM;

EID: 84883240944     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201300356     Document Type: Article

References (97)

1. D. A. Colby, R. G. Bergman, J. A. Ellman, Chem. Rev. 2010, 110, 624
2. T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147
3. C.-L. Sun, B.-J. Li, Z.-J. Shi, Chem. Commun. 2010, 46, 677
4. L. Ackermann, R. Vicente, A. R. Kapdi, Angew. Chem. 2009, 121, 9976
5. Angew. Chem. Int. Ed. 2009, 48, 9792
6. X. Chen, K. M. Engle, D.-H. Wang, J.-Q. Yu, Angew. Chem. 2009, 121, 5196
7. Angew. Chem. Int. Ed. 2009, 48, 5094
8. A. A. Kulkarni, O. Daugulis, Synthesis 2009, 4087
9. F. Kakiuchi, T. Kochi, Synthesis 2008, 3013
10. S. H. Cho, J. Y. Kim, J. Kwak, S. Chang, Chem. Soc. Rev. 2011, 40, 5068
11. J. Wencel-Delord, T. Dröge, F. Liu, F. Glorius, Chem. Soc. Rev. 2011, 40, 4740
12. T. Newhouse, P. S. Baran, Angew. Chem. 2011, 123, 3422
13. Angew. Chem. Int. Ed. 2011, 50, 3362
14. L. Ackermann, Chem. Rev. 2011, 111, 1315
15. L. McMurray, F. O'Hara, M. J. Gaunt, Chem. Soc. Rev. 2011, 40, 1885
16. C. S. Yeung, V. M. Dong, Chem. Rev. 2011, 111, 1215
17. G. Song, F. Wang, X. Li, Chem. Soc. Rev. 2012, 41, 3651
18. K. M. Engle, T.-S. Mei, M. Wasa, J.-Q. Yu, Acc. Chem. Res. 2012, 45, 788
19. J. Yamaguchi, A. D. Yamaguchi, K. Itami, Angew. Chem. 2012, 124, 9092
20. Angew. Chem. Int. Ed. 2012, 51, 8960
21. S. R. Neufeldt, M. S. Sanford, Acc. Chem. Res. 2012, 45, 936
22. N. Kuhl, M. N. Hopkinson, J. Wencel-Delord, F. Glorius, Angew. Chem. 2012, 124, 10382
23. Angew. Chem. Int. Ed. 2012, 51, 10236.
24. N. Li, Z. Yin, X. Jiang, P. Sun, J. Org. Chem. 2011, 76, 8543
25. H. Zhou, Y. H. Xu, W. J. Chung, T. P. Loh, Angew. Chem. 2009, 121, 5459
26. Angew. Chem. Int. Ed. 2009, 48, 5355
27. Z. Liang, B. Yao, Y. Zhang, Org. Lett. 2010, 12, 3185
28. S. D. Yang, B. J. Li, X. B. Wan, Z. J. Shi, J. Am. Chem. Soc. 2007, 129, 6066.
29. K. Fagnou, M. Lautens, Chem. Rev. 2003, 103, 169.
30. K. Chen, H. Li, Y. Li, X.-S. Zhang, Z.-Q. Lei, Z.-J. Shi, Chem. Sci. 2012, 3, 1645
31. J. Wencel-Delord, C. Nimphius, F. W. Patureau, F. Glorius, Angew. Chem. 2012, 124, 2290
32. Angew. Chem. Int. Ed. 2012, 51, 2247.
33. S. M. Raders, J. V. Kingston, J. G. Verkade, J. Org. Chem. 2010, 75, 1744
34. H. M. Lee, S. P. Nolan, Org. Lett. 2000, 2, 2053
35. Z. S. Gu, L.-X. Shao, J.-M. Lu, J. Organomet. Chem. 2012, 700, 132.
36. H. Hachiya, K. Hirano, T. Satoh, M. Miura, Angew. Chem. 2010, 122, 2248
37. Angew. Chem. Int. Ed. 2010, 49, 2202.
38. M. E. Mowery, P. DeShong, Org. Lett. 1999, 1, 2137
39. M. E. Mowery, P. DeShong, J. Org. Chem. 1999, 64, 1684
40. M. E. Mowery, P. DeShong, J. Org. Chem. 1999, 64, 3266
41. M.-R. Brescia, P. DeShong, J. Org. Chem. 1998, 63, 3156
42. A. S. Pilcher, P. DeShong, J. Org. Chem. 1996, 61, 6901
43. S. E. Denmark, Z. Wu, Org. Lett. 1999, 1, 1495
44. S. E. Denmark, J. Y. Choi, J. Am. Chem. Soc. 1999, 121, 5821
45. K. A. Horn, Chem. Rev. 1995, 95, 1317
46. C. Chuit, R. J. P. Corriu, C. Reye, J. C. Young, Chem. Rev. 1993, 93, 1371
47. K. Gouda, E. Hagiwara, Y. Hatanaka, T. Hiyama, J. Org. Chem. 1996, 61, 7232
48. E. Hagiwara, K. Gouda, Y. Hatanaka, T. Hiyama, Tetrahedron Lett. 1997, 38, 439.
49. G.-W. Wang, T. T. Yuan, D.-D. Li, Angew. Chem. 2011, 123, 1416
50. Angew. Chem. Int. Ed. 2011, 50, 1380.
51. J. Karthikeyan, C.-H. Cheng, Angew. Chem. 2011, 123, 10054
52. Angew. Chem. Int. Ed. 2011, 50, 9880.
53. K. H. Dötz, R. Dietz, Chem. Ber. 1978, 111, 2517
54. K. H. Dötz, J. Stendel Jr., in Modern Arene Chemistry (Ed.:, D. Astruc,), Wiley-VCH, Weinheim, 2002, pp. 250 -296.
55. J. Pfeiffer, M. Nieger, K. H. Dötz, Chem. Eur. J. 1998, 4, 1843.
56. K. Tanaka, M. Watanabe, K. Ishibashi, H. Matsuyama, Y. Saikawa, M. Nakata, Org. Lett. 2010, 12, 1700.
57. K. Ueura, T. Satoh, M. Miura, Org. Lett. 2007, 9, 1407
58. N. Umeda, K. Hirano, T. Satoh, M. Miura, J. Org. Chem. 2009, 74, 7094
59. J. Chen, G. Song, C.-L. Pan, X. Li, Org. Lett. 2010, 12, 5426
60. F. W. Patureau, F. Glorius, J. Am. Chem. Soc. 2010, 132, 9982
61. S. Mochida, K. Hirano, T. Satoh, M. Miura, J. Org. Chem. 2011, 76, 3024
62. X. Li, M. Zhao, J. Org. Chem. 2011, 76, 8530
63. A. S. Tsai, M. Brasse, R. G. Bergman, J. A. Ellman, Org. Lett. 2011, 13, 540
64. S. H. Park, J. Y. Kim, S. Chang, Org. Lett. 2011, 13, 2372
65. F. W. Patureau, T. Besset, F. Glorius, Angew. Chem. 2011, 123, 1096
66. Angew. Chem. Int. Ed. 2011, 50, 1064
67. H. Wang, F. Glorius, Angew. Chem. 2012, 124, 7430
68. Angew. Chem. Int. Ed. 2012, 51, 7318
69. P. C. Too, Y.-F. Wang, S. Chiba, Org. Lett. 2010, 12, 5688
70. N. Guimond, K. Fagnou, J. Am. Chem. Soc. 2009, 131, 12050
71. B.-J. Li, H.-Y. Wang, Q.-L. Zhu, Z.-J. Shi, Angew. Chem. 2012, 124, 4014
72. Angew. Chem. Int. Ed. 2012, 51, 3948
73. F. W. Patureau, J. Wencel-Delord, F. Glorius, Aldrichimica Acta 2012, 45, 31
74. T. Satoh, M. Miura, Chem. Eur. J. 2010, 16, 11212.
75. J. Karthikeyan, R. Haridharan, C.-H. Cheng, Angew. Chem. 2012, 124, 12509
76. Angew. Chem. Int. Ed. 2012, 51, 12343.
77. K. Parthasarathy, M. Jeganmohan, C.-H. Cheng, Org. Lett. 2008, 10, 325
78. V. S. Thirunavukkarasu, K. Parthasarathy, C.-H. Cheng, Angew. Chem. 2008, 120, 9604
79. Angew. Chem. Int. Ed. 2008, 47, 9462
80. V. S. Thirunavukkarasu, K. Parthasarathy, C.-H. Cheng, Chem. Eur. J. 2010, 16, 1436
81. P. Gandeepan, K. Parthasarathy, C.-H. Cheng, J. Am. Chem. Soc. 2010, 132, 8569
82. K. Muralirajan, K. Parthasarathy, C.-H Cheng, Angew. Chem. 2011, 123, 4255
83. Angew. Chem. Int. Ed. 2011, 50, 4169
84. J. Jayakumar, K. Parthasarathy, C.-H. Cheng, Angew. Chem. 2012, 124, 201
85. Angew. Chem. Int. Ed. 2012, 51, 197
86. P. Gandeepan, C.-H. Cheng, J. Am. Chem. Soc. 2012, 134, 5738
87. K. Muralirajan, K. Parthasarathy, C.-H. Cheng, Org. Lett. 2012, 14, 4262
88. P. Gandeepan, C.-H. Hung, C.-H. Cheng, Chem. Commun. 2012, 48, 9379.
89. K. Parthasarathy, N. Senthilkumar, J. Jayakumar, C.-H. Cheng, Org. Lett. 2012, 14, 3478
90. K. Padala, S. Pimparkar, P. Madasamy, M. Jeganmohan, Chem. Commun. 2012, 48, 7140.
91. E. M. Simmons, J. F. Hartwig, Angew. Chem. Int. Ed. 2012, 51, 3066.
92. A. J. Hickman, M. S. Sanford, Nature 2012, 484, 177
93. K. Muniz, Angew. Chem. 2009, 121, 9576
94. Angew. Chem. Int. Ed. 2009, 48, 9412.
95. C.-L. Sun, N. Liu, B.-J. Li, D.-G. Yu, Y. Wang, Z.-J. Shi, Org. Lett. 2010, 12, 184.
96. D. D. Perrin, W. L. F. Armarego, in Purification of Laboratory Chemicals, 3 rd ed., Pergamon, New York, 1988.
97. A. S. Manoso, C. Ahn, A. Soheili, C. J. Handy, R. Correia, W. M. Seganish, P. DeShong, J. Org. Chem. 2004, 69, 8305.