Amino-directed RhIII-catalyzed C-H activation leading to one-pot synthesis of N-H carbazoles

Chemistry - A European Journal

Volumn 19, Issue 6, 2013, Pages 1903-1907

  Jiang, Qibai ^a   Duan Mu, Dandan ^a   Zhong, Wei ^a   Chen, Hao ^a   Yan, Hong ^a  

^a NANJING UNIVERSITY   (China)

Author keywords

amino directed; boranes; C H activation; C N formation; homogeneous catalysis; rhodium

Indexed keywords

AMINO-DIRECTED; BORANES; C-H ACTIVATION; C-N FORMATION; HOMOGENEOUS CATALYSIS;

BORON COMPOUNDS; FUNCTIONAL GROUPS; POLYCYCLIC AROMATIC HYDROCARBONS; REACTION KINETICS; RHODIUM;

ACTIVATION ANALYSIS;

AMINE; CARBAZOLE DERIVATIVE; PALLADIUM; RHODIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGEN BOND; SYNTHESIS;

AMINES; CARBAZOLES; CATALYSIS; HYDROGEN BONDING; MOLECULAR STRUCTURE; PALLADIUM; RHODIUM;

EID: 84873293934     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201203856     Document Type: Article

References (130)

1. J. J.; Neumann, S. Rakshit, F. Glorius, Angew. Chem. 2009, 121, 7024 Liu, R. Horst, V. Katritch, R. C. Stevens, K. Wüthrich
2. Science 2012, 335, 1106
3. D. M. Rosenbaum, V. Cherezov, M. A. Hanson, S. G. F. Rasmussen, F. S. Thian, T. S. Kobilka, H. Choi, X. Yao, W. I. Weis, R. C. Stevens, B. K. Kobilka, Science 2007, 318, 1266
4. T. Takeuchi, S. Oishi, T. Watanabe, H. Ohno, J.-I. Sawada, K. Matsuno, A. Asai, N. Asada, K. Kitaura, N. Fujii, J. Med. Chem. 2011, 54, 4839
5. S. Oishi, T. Watanabe, J.-i. Sawada, A. Asai, H. Ohno, N. Fujii, J. Med. Chem. 2010, 53, 5054
6. J. Cheng, K. Kamiya, I. Kodama, Cardiovasc. Drug Rev. 2001, 19, 152
7. C. Sánchez, C. Mèndez, J. Salas, Nat. Prod. Rep. 2006, 23, 1007.
8. Z. M. Hudson, Z.-H. Lu, S. Wang, Adv. Mater. 2012, 24, 2922
9. D. Kim, V. Coropceanu, J.-L. Brédas, J. Am. Chem. Soc. 2011, 133, 17895
10. A. D. Finke, D. E. Gross, A. Han, J. S. Moore, J. Am. Chem. Soc. 2011, 133, 14063
11. F. A. Lemasson, W. Wenzel, M. M. Kappes, M. Mayor, J. Am. Chem. Soc. 2011, 133, 652
12. K. Albrecht, K. Yamamoto, J. Am. Chem. Soc. 2009, 131, 2244
13. N. Blouin, A. Michaud, D. Gendron, D. Wakim, B. Blair, R. Neagu-Plesu, M. Belletete, G. Durocher, Y. Tao, M. Leclerc, J. Am. Chem. Soc. 2008, 130, 732.
14. A. W. Schmidt, K. R. Reddy, H. J. Knölker, Chem. Rev. 2012, 112, 3193, and the references therein
15. J. F. Hartwig, Angew. Chem. 1998, 110, 2154
16. Angew. Chem. Int. Ed. 1998, 37, 2046
17. T. Ogata, J. F. Hartwig, J. Am. Chem. Soc. 2008, 130, 13848
18. L. Ackermann, A. Althammer, Angew. Chem. 2007, 119, 1652
19. Angew. Chem. Int. Ed. 2007, 46, 1627
20. T. Tsuchimoto, H. Matsubayashi, M. Kaneko, Y. Nagase, T. Miyamura, E. Shirakawa, J. Am. Chem. Soc. 2008, 130, 15823
21. Z. Shi, S. Ding, Y. Cui, N. Jiao, Angew. Chem. 2009, 121, 8035
22. Angew. Chem. Int. Ed. 2009, 48, 7895
23. A. P. Antonchick, R. Samanta, K. Kulikov, J. Lategahn, Angew. Chem. 2011, 123, 8764
24. Angew. Chem. Int. Ed. 2011, 50, 8605
25. S. V. Ley, A. W. Thomas, Angew. Chem. 2003, 115, 5558
26. Angew. Chem. Int. Ed. 2003, 42, 5400.
27. Metal-Catalyzed Cross-Coupling Reactions (Eds.:, F. Dieterich, P. J. Stang,), Wiley-VCH, Weinheim, 1998
28. M. Leblanc, K. Fagnou, Org. Lett. 2005, 7, 2849
29. L.-C. Campeau, M. Parisien, A. Jean, K. Fagnou, J. Am. Chem. Soc. 2006, 128, 518
30. M. Parisien, D. Valette, K. Fagnou, J. Org. Chem. 2005, 70, 7578.
31. D. S. Surry, S. L. Buchwald, Angew. Chem. 2008, 120, 6438
32. Angew. Chem. Int. Ed. 2008, 47, 6338
33. J. García-Fortanet, F. Kessler, S. L. Buchwald, J. Am. Chem. Soc. 2009, 131, 6676
34. W. C. P. Tsang, R. H. Munday, B. Gordon, N. Zheng, S. L. Buchwald, J. Org. Chem. 2008, 73, 7603
35. W. C. P. Tsang, N. Zheng, S. L. Buchwald, J. Am. Chem. Soc. 2005, 127, 14560.
36. J. A. Jordan-Hore, C. C. C. Johansson, M. Gulias, E. M. Beck, M. J. Gaunt, J. Am. Chem. Soc. 2008, 130, 16184.
37. J. J.; Neumann, S. Rakshit, F. Glorius, Angew. Chem. 2009, 121, 7024
38. Angew. Chem. Int. Ed. 2009, 48, 6892
39. B.-J. Li, S.-L. Tian, F. Zhao, Z.-J. Shi, Angew. Chem. 2008, 120, 1131
40. Angew. Chem. Int. Ed. 2008, 47, 1115
41. S. W. Youn, J. H. Bihn, B. S. Kim, Org. Lett. 2011, 13, 3738
42. R. Bautista, P. Bernal, L. E. Montiel, F. Delgado, J. Tamariz, Synthesis 2011, 929
43. S. H. Cho, J. Yoon, S. Chang, J. Am. Chem. Soc. 2011, 133, 5996
44. J.-H. Chu, P.-S. Lin, M.-J. Wu, Chem. Eur. J. 2011, 17, 13613
45. D. Kajiyama, K. Inoue, Y. Ishikawa, S. Nishiyama, Tetrahedron 2010, 66, 9779
46. R. Samanta, K. Kulikov, C. Strohmann, A. P. Antonchick, Synthesis 2012, 2325.
47. B. J. Stokes, K. J. Richert, T. G. Driver, J. Org. Chem. 2009, 74, 6442
48. B. J. Stokes, H. Dong, K. J. Richert, R. D. Riell, T. G. Driver, J. Org. Chem. 2009, 74, 3225
49. W. G. Shou, J. Li, T. Guo, Z. Lin, G. Jia, Organometallics 2009, 28, 6847.
50. T. Horaguchi, T. J. Oyanagi, Heterocycl. Chem. 2004, 41, 1
51. S. Matsubara, K. Asano, Y. Kajita, M. Yamamoto, Synthesis 2007, 2055
52. M. Yamamoto, S. Matsubara, Chem. Lett. 2007, 36, 172.
53. H.-X. Dai, J.-Q. Yu, J. Am. Chem. Soc. 2012, 134, 134
54. C. C. Tzschucke, J. M. Murphy, J. F. Hartwig, Org. Lett. 2007, 9, 761
55. F. Bellina, R. Rossi, Adv. Synth. Catal. 2010, 352, 1223
56. P. Y. S. Lam, C. G. Clark, Tetrahedron Lett. 1998, 39, 2941
57. T. D. Quach, R. A. Batey, Org. Lett. 2003, 5, 4397
58. D. M. T. Chan, K. L. Monaco, R.-P. Wang, M. P. Winters, Tetrahedron Lett. 1998, 39, 2933
59. S. Chen, H. Huang, X. Liu, J. Shen, H. Jiang, H. Liu, J. Comb. Chem. 2008, 10, 358
60. B. Kaboudin, Y. Abedi, T. Yokomatsu, Eur. J. Org. Chem. 2011, 6656.
61. D. A. Colby, A. S. Tsai, R. G. Bergman, J. A. Ellman, Acc. Chem. Res. 2012, 45, 814
62. D. A. Colby, R. G. Bergman, J. A. Ellman, Chem. Rev. 2010, 110, 624
63. P. B. Arockiam, C. Bruneau, P. H. Dixneuf, Chem. Rev. 2012, 112, 5879
64. J. Wencel-Delord, F. Glorius, Chem. Soc. Rev. 2011, 40, 4740
65. T. Brückl, R. D. Baxter, Y. Ishihara, P. S. Baran, Acc. Chem. Res. 2012, 45, 826
66. B.-J. Li, Z.-J. Shi, Chem. Soc. Rev. 2012, 41, 5588
67. S. R. Neufeldt, M. S. Sanford, Acc. Chem. Res. 2012, 45, 936
68. J. C. Lewis, R. G. Bergman, J. A. Ellman, Acc. Chem. Res. 2008, 41, 1013
69. C. Jia, T. Kitamura, Y. Fujiwara, Acc. Chem. Res. 2001, 34, 633
70. M. S. Sigman, E. W. A. Werner, Acc. Chem. Res. 2012, 45, 874
71. M. M. Díaz-Requejo, P. J. Pérez, Chem. Rev. 2008, 108, 3379
72. R. H. Crabtree, Chem. Rev. 2012, 112, 1536
73. K. M. Engle, T. Mei, M. Wasa, J.-Q. Yu, Acc. Chem. Res. 2012, 45, 788
74. S. H. Cho, J. Y. Kim, J. Kwak, S. Chang, Chem. Soc. Rev. 2011, 40, 5068
75. C. Liu, H. Zhang, W. Shi, A. Lei, Chem. Rev. 2011, 111, 1780
76. C.-J. Li, Acc. Chem. Res. 2009, 42, 335
77. C.-L. Sun, Z.-J. Shi, Chem. Rev. 2011, 111, 1293
78. G. Song, F. Wang, X. Li, Chem. Soc. Rev. 2012, 41, 3651.
79. E. Ferrer Flegeau, C. Bruneau, P. H. Dixneuf, A. Jutand, J. Am. Chem. Soc. 2011, 133, 10161
80. D. Leow, G. Li, T. S. Mei, J.-Q. Yu, Nature 2012, 486, 518
81. L. Li, W. D. Jones, J. Am. Chem. Soc. 2008, 130, 12414
82. L. Li, W. D. Jones, J. Am. Chem. Soc. 2007, 129, 10707
83. T. Newhouse, P. S. Baran, Angew. Chem. 2011, 123, 3422
84. Angew. Chem. Int. Ed. 2011, 50, 3362
85. N. Schröder, F. Glorius, J. Am. Chem. Soc. 2012, 134, 8298
86. J. Wencel-Delord, C. Nimphius, F. W. Patureau, F. Glorius, Angew. Chem. 2012, 124, 2290
87. Angew. Chem. Int. Ed. 2012, 51, 2247
88. H. Wang, F. Glorius, Angew. Chem. 2012, 124, 7430
89. B.-J. Li, H.-Y. Wang, Q.-L. Zhu, Z.-J. Shi, Angew. Chem. 2012, 124, 4014
90. Angew. Chem. Int. Ed. 2012, 51, 3948
91. H. Du, B. Zhao, Y. Shi, J. Am. Chem. Soc. 2008, 130, 8590
92. B. Wang, H. Du, Y. Shi, Angew. Chem. 2008, 120, 8348
93. Angew. Chem. Int. Ed. 2008, 47, 8224
94. K. Muralirajan, K. Parthasarathy, C. H. Cheng, Angew. Chem. 2011, 123, 4255
95. Angew. Chem. Int. Ed. 2011, 50, 4169
96. N. Guimond, S. I. Gorelsky, K. Fagnou, J. Am. Chem. Soc. 2011, 133, 6449
97. D. R. Stuart, P. Alsabeh, M. Kuhn, K. Fagnou, J. Am. Chem. Soc. 2010, 132, 18326.
98. I. A. Mkhalid, J. H. Barnard, T. B. Marder, J. M. Murphy, J. F. Hartwig, Chem. Rev. 2010, 110, 890 and the references therein
99. J. F. Hartwig, Acc. Chem. Res. 2012, 45, 864
100. H. Chen, S. Schlecht, T. C. Semple, J. F. Hartwig, Science 2000, 287, 1995
101. C. N. Iverson, M. R. Smith III., J. Am. Chem. Soc. 1999, 121, 7696
102. J.-Y. Cho, M. K. Tse, D. Holmes, R. E., Jr. Maleczka, M. R. Smith III., Science 2002, 295, 305
103. J.-Y. Cho, C. N. Iverson, M. R. Smith III., J. Am. Chem. Soc. 2000, 122, 12868
104. P. C. Roosen, V. A. Kallepalli, B. Chattopadhyay, D. A. Singleton, R. E., Jr. Maleczka, M. R. Smith III., J. Am. Chem. Soc. 2012, 134, 11350.
105. S. Shimada, A. S. Batsanov, J. A. K. Howard, T. B. Marder, Angew. Chem. 2001, 113, 2226
106. Angew. Chem. Int. Ed. 2001, 40, 2168
107. S. Kawamorita, H. Ohmiya, K. Hara, A. Fukuoka, M. Sawamura, J. Am. Chem. Soc. 2009, 131, 5058
108. T. Ishiyama, H. Isou, T. Kikuchi, N. Miyaura, Chem. Commun. 2010, 46, 159
109. K. Yamazaki, S. Kawamorita, H. Ohmiya, M. Sawamura, Org. Lett. 2010, 12, 3978
110. H. Itoh, T. Kikuchi, T. Ishiyama, N. Miyaura, Chem. Lett. 2011, 40, 1007
111. A. Ros, B. Estepa, R. López-Rodríguez, E. Álvarez, R. Fernández, J. M. Lassaletta, Angew. Chem. 2011, 123, 11928
112. Angew. Chem. Int. Ed. 2011, 50, 11724
113. S. Kawamorita, T. Miyazaki, H. Ohmiya, T. Iwai, M. Sawamura, J. Am. Chem. Soc. 2011, 133, 19310
114. N. Selander, B. Willy, K. J. Szabo, Angew. Chem. 2010, 122, 4145
115. Angew. Chem. Int. Ed. 2010, 49, 4051
116. M. Tobisu, H. Kinuta, N. Chatani, J. Am. Chem. Soc. 2012, 134, 115.
117. K. Morimoto, M. Itoh, K. Hirano, T. Satoh, M. Miura, Angew. Chem. 2012, 124, 5455
118. Angew. Chem. Int. Ed. 2012, 51, 5359
119. D.-D. Li, T.-T. Yuan, G.-W. Wang, J. Org. Chem. 2012, 77, 3341
120. F. Patureau, T. Besset, F. Glorius, Angew. Chem. 2011, 123, 1096
121. Angew. Chem. Int. Ed. 2011, 50, 1064.
122. Z. Liang, L. Ju, Y.-J. Xie, L.-H. Huang, Y.-H. Zhang, Chem. Eur. J. 2012, 18, 15816
123. K.-Y. Ye, H. He, W.-B. Liu, L.-X. Dai, G. Helmchen, S.-L. You, J. Am. Chem. Soc. 2011, 133, 19006
124. H. He, W.-B. Liu, L.-X. Dai, S.-L. You, J. Am. Chem. Soc. 2009, 131, 8346.
125. Y. Y. Kok, L. Y. Mooi, A. M. Ali, Molecules 2012, 17, 4651.
126. T. Nagappan, C. S. Vairappan, Molecules 2011, 16, 9651
127. S. Pandit, P. K. Mukherjee, Biomed. Chromatogr. 2011, 25, 959.
128. T.-S. Wu, Y.-Y. Chan, M.-J. Liou, F.-W. Lin, L.-S. Shi, K.-T. Chen, Phytother. Res. 1998, 12, S 80.
129. H.-J. Knölker, K. R. Reddy, Chem. Rev. 2002, 102, 4303
130. R. Forker, M. P. Krahl, F. Däbritz, A. Jäger, H.-J. Knölker, Synlett 2008, 1870.