RhIII-catalyzed redox-neutral C-H activation of pyrazolones: An economical approach for the synthesis of N-substituted indoles

Organic Letters

Volumn 17, Issue 2, 2015, Pages 310-313

  Fan, Zhoulong ^a   Song, Shanshan ^a   Li, Wei ^b   Geng, Kaijun ^a   Xu, Youjun ^b   Miao, Ze Hong ^a   Zhang, Ao ^a  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

^b SHENYANG PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; PYRAZOLONE DERIVATIVE; RHODIUM;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGEN BOND; OXIDATION REDUCTION REACTION; SYNTHESIS;

CATALYSIS; HYDROGEN BONDING; INDOLES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PYRAZOLONES; RHODIUM;

EID: 84921371594     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol503404p     Document Type: Article

References (75)

1. Kochanowska-Karamyan, A. J.; Hamann, M. T. Chem. Rev. 2010, 110, 4489
2. Lalit, K.; Shashi, B.; Kamal, J. Int. J. Res. Pharm. Sci. 2012, 2, 23
3. Biswal, S.; Sahoo, U.; Sethy, S.; Kumar, H. K. S.; Banerjee, M. Asian J. Pharm. Clin. Res. 2012, 5, 1
4. Randey, R.; Swamy, K. V.; Khetmalas, M. B. Indian J. Biotechnol. 2013, 12, 297
5. Ates-Alagoz, Z. Curr. Med. Chem. 2013, 20, 4633
6. Patil, S. A.; Patil, R.; Miller, D. D. Future Med. Chem. 2012, 4, 2085
7. Biersack, B.; Schobert, R. Curr. Drug Targets 2012, 13, 1705
8. Li, X.; Li, J.-R.; Chen, K.; Zhu, H.-L. Curr. Med. Chem. 2013, 20, 3903
9. Ahmad, A.; Biersack, B.; Li, Y.; Kong, D.; Bao, B.; Schobert, R.; Padhye, S. B.; Sarkar, F. H. Anticancer Agents Med. Chem. 2013, 13, 1002
10. Xu, H.; Lv, M. Curr. Pharm. Des. 2009, 15, 2120
11. Ölgen, S. Mini-Rev. Med. Chem. 2013, 13, 1700
12. Skaltsounis, A.-L.; Gaboriaud-Kolar, N. Expert Opin. Ther. Pat. 2011, 21, 1925
13. Gribble, G. W. J. Chem. Soc., Perkin Trans. 1 2000, 1045
14. Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2873
15. Humphrey, G. R.; Kuethe, J. T. Chem. Rev. 2006, 106, 2875
16. Song, J. J.; Reeves, J. T.; Gallou, F.; Tan, Z.; Yee, N. K.; Senanayake, C. H. Chem. Soc. Rev. 2007, 36, 1120
17. Song, J. J.; Reeves, J. T.; Fandrick, D. R.; Tan, Z.; Yee, N. K.; Senanayake, C. H. ARKIVOC 2010, i, 390
18. Cacchi, S.; Fabrizi, G. Chem. Rev. 2011, 111, PR215
19. Vicente, R. Org. Biomol. Chem. 2011, 9, 6469
20. Platon, M.; Amardeil, R.; Djakovitch, L.; Hierso, J.-C. Chem. Soc. Rev. 2012, 41, 3929
21. Mérour, J.-Y.; Routier, S.; Suzenet, F.; Joseph, B. Tetrahedron 2013, 69, 4767
22. Inman, M.; Moody, C. J. Chem. Sci. 2013, 4, 29
23. Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094
24. Ackermann, L.; Vicente, R.; Kapdi, A. R. Angew. Chem., Int. Ed. 2009, 48, 9792
25. Thansandote, P.; Mark Lautens, M. Chem.-Eur. J. 2009, 15, 5874
26. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
27. Satoh, T.; Miura, M. Chem.-Eur. J. 2010, 16, 11212
28. McMurray, L.; O'Hara, F.; Gaunt, M. J. Chem. Soc. Rev. 2011, 40, 1885
29. Wencel-Delord, J.; Dröge, T.; Liu, F.; Glorius, F. Chem. Soc. Rev. 2011, 40, 4740
30. Ackermann, L. Chem. Rev. 2011, 111, 1315
31. Li, B.-J.; Shi, Z.-J. Chem. Soc. Rev. 2012, 41, 5588
32. Song, G.; Wang, F.; Li, X. Chem. Soc. Rev. 2012, 41, 3651
33. Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689
34. Shen, M.; Li, G. S.; Lu, B. Z.; Hossain, A.; Roschangar, F.; Farina, V.; Senanayake, C. H. Org. Lett. 2004, 6, 4129
35. Nakamura, I.; Nemoto, T.; Shiraiwa, N.; Terada, M. Org. Lett. 2009, 11, 1055
36. Phetrak, N.; Rukkijakan, T.; Sirijaraensre, J.; Prabpai, S.; Kongsaeree, P.; Klinchan, C.; Chuawong, P. J. Org. Chem. 2013, 78, 12703
37. Stuart, D. R.; Bertrand-Laperle, M.; Burgess, K. M. N.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 16474
38. Stuart, D. R.; Alsabeh, P.; Kuhn, M.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 18326
39. Song, W.; Ackermann, L. Chem. Commun. 2013, 49, 6638
40. Zhang, G.; Yu, H.; Qin, G.; Huang, H. Chem. Commun. 2014, 50, 4331
41. Hoshino, Y.; Shibata, Y.; Tanaka, K. Adv. Synth. Catal. 2014, 356, 1577
42. Chen, J.; He, L.; Natte, K.; Neumann, H.; Beller, M.; Wu, X.-F. Adv. Synth. Catal. 2014, 356, 2955
43. Kathiravan, S.; Nicholls, I. A. Chem. Commun. 2014, 50, 14964
44. Richter, J. M.; Ishihara, Y.; Masuda, T.; Whitefield, B. W.; Llamas, T.; Pohjakallio, A.; Baran, P. S. J. Am. Chem. Soc. 2008, 130, 17938
45. Wu, J.; Cui, X.; Chen, L.; Jiang, G.; Wu, Y. J. Am. Chem. Soc. 2009, 131, 13888
46. Tan, Y.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 3676
47. Guimond, N.; Gouliaras, C.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 6908
48. Guimond, N.; Gorelsky, S. I.; Fagnou, K. J. Am. Chem. Soc. 2011, 133, 6449
49. Patureau, F. W.; Glorius, F. Angew. Chem., Int. Ed. 2011, 50, 1977
50. Li, B.; Feng, H.; Xu, S.; Wang, B. Chem.-Eur. J. 2011, 17, 12573
51. Hyster, T. K.; Rovis, T. Chem. Commun. 2011, 47, 11846
52. Liu, G.; Shen, Y.; Zhou, Z.; Lu, X. Angew. Chem., Int. Ed. 2013, 52, 6033
53. Neely, J. M.; Rovis, T. J. Am. Chem. Soc. 2013, 135, 66
54. Chinnagolla, R. K.; Pimparkar, S.; Jeganmohan, M. Org. Lett. 2012, 14, 3032
55. Zhu, C.; Yamane, M. Tetrahedron 2011, 67, 4933
56. Wang, C.; Sun, H.; Fang, Y.; Huang, Y. Angew. Chem., Int. Ed. 2013, 52, 5795
57. Zhao, D.; Shi, Z.; Glorius, F. Angew. Chem., Int. Ed. 2013, 52, 12426
58. Liu, B.; Song, C.; Sun, C.; Zhou, S.; Zhu, J. J. Am. Chem. Soc. 2013, 135, 16625
59. Wang, C.; Huang, Y. Org. Lett. 2013, 15, 5294
60. Chuang, S.-C.; Gandeepan, P.; Cheng, C.-H. Org. Lett. 2013, 15, 5750
61. Huang, X.-C.; Yang, X.-H.; Song, R.-J.; Li, J.-H. J. Org. Chem. 2014, 79, 1025
62. Zheng, L.; Hua, R. Chem.-Eur. J. 2014, 20, 2352
63. Fang, Y.; Wang, C.; Su, S.; Yu, H.; Huang, Y. Org. Biomol. Chem. 2014, 12, 1061
64. Muralirajana, K.; Cheng, C.-H. Adv. Synth. Catal. 2014, 356, 1571
65. Trost, B. M. Science 1991, 254, 1471
66. Wender, P. A.; Miller, B. L. In Organic Synthesis: Theory and Application; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1993; Vol. 2.
67. Wender, P. A.; Verma, V. A.; Paxton, T. J.; Pillow, T. H. Acc. Chem. Res. 2008, 41, 40
68. Newhouse, T.; Baran, P. S.; Hoffmann, R. W. Chem. Soc. Rev. 2009, 38, 3010
69. Trost, B. M.; Yang, H.; Brindle, C. S.; Dong, G. Chem.-Eur. J. 2011, 17, 9777
70. Fan, Z.; Wu, K.; Xing, L.; Yao, Q.; Zhang, A. Chem. Commun. 2014, 50, 1682
71. Xing, L.; Fan, Z.; Hou, C.; Yong, G.; Zhang, A. Adv. Synth. Catal. 2014, 356, 972
72. Wu, K.; Fan, Z.; Xue, Y.; Yao, Q.; Zhang, A. Org. Lett. 2014, 16, 42
73. Zhang, Z.; Jiang, H.; Huang, Y. Org. Lett. 2014, 16, 5976
74. Dong, W.; Wang, L.; Parthasarathy, K.; Pan, F.; Bolm, C. Angew. Chem., Int. Ed. 2013, 52, 11573
75. Xu, L.; Zhu, Q.; Huang, G.; Cheng, B.; Xia, Y. J. Org. Chem. 2012, 77, 3017