Rhodium(III)-catalyzed hydrazine-directed C-H activation for indole synthesis: Mechanism and role of internal oxidant probed by DFT studies

Organometallics

Volumn 34, Issue 1, 2015, Pages 309-318

  Chen, Wen Jie ^a   Lin, Zhenyang ^a  

^a HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ANALYSIS; CATALYSIS; CHEMICAL ACTIVATION; HYDRAZINE; HYDROCARBONS; OXIDANTS; SYNTHESIS (CHEMICAL);

ACTIVE SPECIES; ALKYNE INSERTIONS; C-H ACTIVATION; CALCULATION RESULTS; CATALYTIC CYCLES; CATALYTIC REACTIONS; DFT CALCULATION; REACTION MECHANISM;

RHODIUM;

EID: 84921065369     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om501130c     Document Type: Article

References (75)

1. Sundberg, R. J. Indoles; Academic Press: San Diego, CA, 1996.
2. Somei, M.; Yamada, F. Nat. Prod. Rep. 2004, 21, 278
3. Somei, M.; Yamada, F. Nat. Prod. Rep. 2005, 22, 73
4. de Sá Alves, F. R.; Barreiro, E. J.; Fraga, C. A. M. Mini-Rev. Med. Chem. 2009, 9, 782
5. Kochanowska-Karamyan, A. J.; Hamann, M. T. Chem. Rev. 2010, 110, 4489
6. Patil, S. A.; Patil, R.; Miller, D. D. Future Med. Chem. 2012, 4, 2085
7. Ishikura, M.; Abe, T.; Choshi, T.; Hibin, S. Nat. Prod. Rep. 2013, 30, 694
8. Inman, M.; Moody, C. J. Chem. Sci. 2013, 4, 29
9. Zeni, G.; Larock, R. C. Chem. Rev. 2004, 104, 2285
10. Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2873
11. Humphrey, G. R.; Kuethe, J. T. Chem. Rev. 2006, 106, 2875
12. Ackermann, L. Synlett 2007, 507
13. Krüger, K. (née Alex); Tillack, A.; Beller, M. Adv. Synth. Catal. 2008, 350, 2153
14. Patil, N. T.; Yamamoto, Y. Chem. Rev. 2008, 108, 3395
15. Bandini, M.; Eichholzer, A. Angew. Chem., Int. Ed. 2009, 48, 9608
16. Cacchi, S.; Fabrizi, G. Chem. Rev. 2011, 111, 215
17. Shiri, M. Chem. Rev. 2012, 112, 3508
18. Shi, Z. Z.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 9220
19. Ackermann, L.; Lygin, A. V. Org. Lett. 2012, 14, 764
20. Wang, C.; Sun, H.; Fang, Y.; Huang, Y. Angew. Chem., Int. Ed. 2013, 52, 5795
21. Stuart, D. R.; Bertrand-Laperle, M.; Burgess, K. M. N.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 16474
22. Stuart, D. R.; Alsabeh, P.; Kuhn, M.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 18326
23. Huestis, M. P.; Chan, L. N.; Stuart, D. R.; Fagnou, K. Angew. Chem., Int. Ed. 2011, 50, 1338
24. Feng, Z.; Han, X. L.; Lu, X. Y. Tetrahedron Lett. 2011, 52, 4681
25. Ackermann, L.; Lygin, A. V. Org. Lett. 2012, 14, 764
26. Würtz, S.; Rakshit, S.; Neumann, J. J.; Dröge, T.; Glorius, F. Angew. Chem., Int. Ed. 2008, 47, 7230
27. Shi, Z.; Zhang, C.; Li, S.; Pan, D.; Ding, S.; Cui, Y.; Jiao, N. Angew. Chem., Int. Ed. 2009, 48, 4572
28. For a highlight, see: Patureau, F. W.; Glorius, F. Angew. Chem., Int. Ed. 2011, 50, 1977
29. Tan, Y.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 3676
30. Wu, J.; Cui, X.; Chen, L.; Jiang, G.; Wu, Y. J. Am. Chem. Soc. 2009, 131, 13888
31. Guimond, N.; Gouliaras, C.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 6908
32. Guimond, N.; Gorelsky, S. I.; Fagnou, K. J. Am. Chem. Soc. 2011, 133, 6449
33. Wang, H.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 7318
34. Rakshit, S.; Grohmann, C.; Besset, T.; Glorius, F. J. Am. Chem. Soc. 2011, 133, 2350
35. Hyster, T. K.; Rovis, T. Chem. Commun. 2011, 47, 11846
36. Hyster, T. K.; Knörr, L.; Ward, T. R.; Rovis, T. Science 2012, 338, 500
37. Neely, J. M.; Rovis, T. J. Am. Chem. Soc. 2013, 135, 66
38. Too, P. C.; Wang, Y.-F.; Chiba, S. Org. Lett. 2010, 12, 5688
39. Too, P. C.; Noji, T.; Lim, Y. J.; Li, X.; Chiba, S. Synlett 2011, 2789
40. Too, P. C.; Chua, S. H.; Wong, S. H.; Chiba, S. J. Org. Chem. 2011, 76, 6159
41. Li, B.; Feng, H.; Xu, S.; Wang, B. Chem. Eur. J. 2011, 17, 12573
42. Li, B.; Ma, J.; Wang, N.; Feng, H.; Xu, S.; Wang, B. Org. Lett. 2012, 14, 736
43. Ackermann, L.; Fenner, S. Org. Lett. 2011, 13, 6548
44. Chinnagolla, R. K.; Pimparkar, S.; Jeganmohan, M. Org. Lett. 2012, 14, 3032
45. Zhao, D.; Shi, Z.; Glorius, F. Angew. Chem., Int. Ed. 2013, 52, 12426
46. Liu, B.; Song, C.; Sun, C.; Zhou, S.; Zhu, J. J. Am. Chem. Soc. 2013, 135, 16625
47. Wang, C.; Huang, Y. Org. Lett. 2013, 15, 5294
48. Zheng, L.; Hua, R. Chem. Eur. J. 2014, 20, 2352
49. Liu, G.; Shen, Y.; Zhou, Z.; Lu, X. Angew. Chem., Int. Ed. 2013, 52, 6033
50. Shen, Y.; Liu, G.; Zhou, Z.; Lu, X. Org. Lett. 2013, 15, 3366
51. Zhao, Y.; Truhlar, D. G. Acc. Chem. Res. 2008, 41, 157
52. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215
53. Truhlar, D. G. J. Am. Chem. Soc. 2008, 130, 16824
54. Zhao, Y.; Truhlar, D. G. J. Chem. Theory Comput. 2009, 5, 324
55. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270
56. Wadt, W. R.; Hay, P. J. J. Chem. Phys. 1985, 82, 284
57. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299
58. Ehlers, A. W.; Böhme, M.; Dapprich, S.; Gobbi, A.; Höllwarth, A.; Jonas, V.; Köhler, K. F.; Stegmenn, R.; Frenking, G. Chem. Phys. Lett. 1993, 208, 111
59. Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257
60. Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213
61. Fukui, K. J. Phys. Chem. 1970, 74, 4161
62. Fukui, K. Acc. Chem. Res. 1981, 14, 363
63. Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B 2009, 113, 6378
64. Grimme, S.; Antony, J.; Ehrlich, S.; Krieg, H. J. Chem. Phys. 2010, 132, 154104
65. Frisch, M. J.; Gaussian 09, revision D.01; Gaussian, Inc., Pittsburgh, PA, 2009.
66. de Marothy, S. A. XYZViewer version 0.97; Stockholm, Sweden, 2010.
67. Margl, P. M.; Deng, L.; Ziegler, T. J. Am. Chem. Soc. 1998, 120, 5517
68. Niu, S.; Hall, M. B. Chem. Rev. 2000, 100, 353
69. Bai, T.; Zhu, J.; Xue, P.; Sung, H. H.-Y.; Williams, I. D.; Ma, S.; Lin, Z.; Jia, G. Organometallics 2007, 26, 5581
70. Li, Y.; Lin, Z. Organometallics 2013, 32, 3003
71. Li, Y.; Lin, Z. J. Org. Chem. 2013, 78, 11357
72. Xu, L.; Zhu, Q.; Huang, J. P.; Cheng, B.; Xia, Y. Z. J. Org. Chem. 2012, 77, 3017
73. Wang, Y.; Wang, J.; Su, J.; Huang, F.; Jiao, L.; Liang, Y.; Yang, D.; Zhang, S.; Wender, P. A.; Yu, Z. X. J. Am. Chem. Soc. 2007, 129, 10060
74. Yu, Z. X.; Wender, P. A.; Houk, K. N. J. Am. Chem. Soc. 2004, 126, 9154
75. Ozawa, F.; Mori, T. Organometallics 2003, 22, 3593