Rh-catalyzed sequential oxidative C-H and N-N bond activation: Conversion of azines into isoquinolines with air at room temperature

Organic Letters

Volumn 16, Issue 13, 2014, Pages 3532-3535

  Han, Wenjia ^b   Zhang, Guoying ^a   Li, Guangxing ^b   Huang, Hanmin ^a  

^a LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

^b HUAZHONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84903749611     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol501483k     Document Type: Article

References (84)

1. Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731
2. Kakiuchi, F.; Murai, S. Acc. Chem, Res. 2002, 35, 826
3. Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174
4. Ackermann, L.; Vicente, R.; Kapdi, A. R. Angew. Chem., Int. Ed. 2009, 48, 9792
5. Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094
6. Daugulis, O.; Do, H.-Q.; Shabashov, D. Acc. Chem. Res. 2009, 42, 1074
7. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
8. Willis, M. C. Chem. Rev. 2010, 110, 725
9. Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev. 2011, 40, 5068
10. Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Rev. 2011, 111, 1293
11. Ackermann, L. Chem. Rev. 2011, 111, 1315
12. Arockiam, P. B.; Bruneau, C.; Dixneuf, P. H. Chem. Rev. 2012, 112, 5879
13. Yang, L.; Huang, H. Catal. Sci. Technol. 2012, 2, 1099
14. Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem., Int. Ed. 2012, 51, 8960
15. Neufeldt, S. R.; Sanford, M. S. Acc. Chem. Res. 2012, 45, 936
16. Wencel-Delord, J.; Glorius, F. Nat. Chem. 2013, 5, 369
17. Lewis, J. C.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2008, 41, 1013
18. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624
19. Bouffard, J.; Itami, K. Top. Curr. Chem. 2010, 292, 231
20. Satoh, T.; Miura, M. Chem.-Eur. J. 2010, 16, 11212
21. Colby, D. A.; Tsai, A. S.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2012, 45, 814
22. Song, G.; Wang, F.; Li, X. Chem. Soc. Rev. 2012, 41, 3651
23. Patureau, F. W.; Wencel-Delord, J.; Glorius, F. Aldrichimica Acta 2012, 45, 31
24. Umeda, N.; Tsurugi, H.; Satoh, T.; Miura, M. Angew. Chem., Int. Ed. 2008, 47, 4019
25. Stuart, D. R.; Alsabeh, P.; Kuhn, M.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 18326
26. Mochida, S.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2011, 76, 3024
27. Li, X.; Zhao, M. J. Org. Chem. 2011, 76, 8530
28. Park, S. H.; Kim, J. Y.; Chang, S. Org. Lett. 2011, 13, 2372
29. Tsai, A. S.; Brasse, M.; Bergman, R. G.; Ellman, J. A. Org. Lett. 2011, 13, 540
30. Umeda, N.; Hirano, K.; Satoh, T.; Shibata, N.; Sato, H.; Miura, M. J. Org. Chem. 2011, 76, 13
31. Fukuyani, T.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2011, 76, 2867
32. Wang, C.; Sun, H.; Fang, Y.; Huang, Y. Angew. Chem., Int. Ed. 2013, 52, 5795
33. Shang, Y.; Jie, X.; Zhao, H.; Hu, P.; Su, W. Org. Lett. 2014, 16, 416
34. Guimond, N.; Fagnou, K. J. Am. Chem. Soc. 2009, 131, 12050
35. Guimond, N.; Gouliaras, C.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 6908
36. Too, P. C.; Wang, Y.-F.; Chiba, S. Org. Lett. 2010, 12, 5688
37. Rakshit, S.; Grohmann, C.; Besset, T.; Glorius, F. J. Am. Chem. Soc. 2011, 133, 2350
38. Patureau, F. W.; Glorius, F. Angew. Chem., Int. Ed. 2011, 50, 1977
39. Wang, Y.-F.; Toh, K. K.; Lee, J.-Y.; Chiba, S. Angew. Chem., Int. Ed. 2011, 50, 5927
40. Hyster, T. K.; Rovis, T. Chem. Commun. 2011, 47, 11846
41. Xu, X.; Liu, Y.; Park, C.-M. Angew. Chem., Int. Ed. 2012, 51, 9506
42. Wang, H.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 7318
43. Wang, H.; Grohmann, C.; Nimphius, C.; Glorius, F. J. Am. Chem. Soc. 2012, 134, 19592
44. Hyster, T. K.; Kncrr, L.; Ward, T. R.; Rovis, T. Science 2012, 338, 500
45. Ye, B.; Cramer, N. Science 2012, 338, 504
46. Zhu, C.; Li, G.; Ess, D. H.; Falck, J. R.; Kürti, L. J. Am. Chem. Soc. 2012, 134, 18253
47. Neely, J. M.; Rovis, T. J. Am. Chem. Soc. 2013, 135, 66
48. Presset, M.; Oehlrich, D.; Rombouts, F.; Molander, G. A. Org. Lett. 2013, 15, 1528
49. Liu, B.; Song, C.; Sun, C.; Zhou, S.; Zhu, J. J. Am. Chem. Soc. 2013, 135, 16625
50. Jat, J. L.; Paudyal, M. P.; Gao, H.; Xu, Q.-L.; Yousufuddin, M.; Devarajan, D.; Ess, D. H.; Kürti, L.; Falck, J. R. Science 2014, 343, 61
51. Fritsch, P. Ber. Dtsch. Chem. Ges. 1893, 26, 419
52. Pomeranz, C. Monatsh. Chem. 1893, 14, 116
53. Bischler, A.; Napieralski, B. Ber. Dtsch. Chem. Ges. 1893, 26, 1903
54. Pictet, A.; Spengler, T. Chem. Ber. 1911, 44, 2030
55. Herz, W.; Tocker, S. J. Am. Chem. Soc. 1955, 77, 6355
56. Brown, E. V. J. Org. Chem. 1977, 42, 3208
57. Ishikawa, T.; Shimooka, K.; Narioka, T.; Noguchi, S.; Saito, T.; Ishikawa, A.; Yamazaki, E.; Harayama, T.; Seki, H.; Yamaguchi, K. J. Org. Chem. 2000, 65, 9143
58. Youn, S. W. J. Org. Chem. 2006, 71, 2521
59. Xu, X.; Guo, S.; Dang, Q.; Chen, J.; Bai, X. J. Comb. Chem. 2007, 9, 773
60. Ohff, A.; Zippel, T.; Arndt, P.; Spannenberg, A.; Kempe, R.; Rosenthal, U. Organometallics 1998, 17, 1649
61. Zippel, T.; Arndt, P.; Ohff, A.; Spannenberg, A.; Kempe, R.; Rosenthal, U. Organometallics 1998, 17, 4429
62. Kiplinger, J. L.; Morris, D. E.; Scott, B. L.; Burns, C. J. Organometallics 2002, 21, 3073
63. Cohen, R.; Rybtchinski, B.; Gandelman, M.; Shimon, L. J. W.; Martin, J. M. L.; Milstein, D. Angew. Chem., Int. Ed. 2003, 115, 1993
64. Umehara, K.; Kuwata, S.; Ikariya, T. J. Am. Chem. Soc. 2013, 135, 6754
65. Zhang, G.; Yang, L.; Wang, Y.; Xie, Y.; Huang, H. J. Am. Chem. Soc. 2013, 135, 8850
66. Yang, L.; Zhang, G.; Huang, H. Adv. Synth. Catal. 2014, 356, 1509
67. Zhang, G.; Yu, H.; Qin, G.; Huang, H. Chem. Commun. 2014, 50, 4331
68. Roesch, K. R.; Larock, R. C. J. Org. Chem. 1998, 63, 5306
69. Roesch, K. R.; Larock, R. C. Org. Lett. 1999, 1, 553
70. Dai, G.; Larock, R. C. Org. Lett. 2002, 4, 193
71. Huang, Q.; Larock, R. C. J. Org. Chem. 2003, 68, 980
72. Konno, T.; Chae, J.; Miyabe, T.; Ishihara, T. J. Org. Chem. 2005, 70, 10172
73. Korivi, R. P.; Cheng, C.-H. Org. Lett. 2005, 7, 5179
74. Fischer, D.; Tomeba, H.; Pahadi, N. K.; Patil, N. T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2007, 46, 4764
75. Li, L.; Brennessel, W. W.; Jones, W. D. J. Am. Chem. Soc. 2008, 130, 12414
76. Fukutani, T.; Umeda, N.; Hirano, K.; Satoh, T.; Miura, M. Chem. Commun. 2009, 5141
77. Hwang, S.; Lee, Y.; Lee, P. H.; Shin, S. Tetrahedron Lett. 2009, 50, 2305
78. Gao, H.; Zhang, J. Adv. Synth. Catal. 2009, 351, 85
79. Jayakumar, J.; Parthasarathy, K.; Cheng, C.-H. Angew. Chem., Int. Ed. 2012, 51, 197
80. Karthikeyan, J.; Haridharan, R.; Cheng, C.-H. Angew. Chem., Int. Ed. 2012, 51, 12343
81. Huang, X.-C.; Yang, X.-H.; Song, R.-J.; Li, J.-H. J. Org. Chem. 2014, 79, 1025
82. CCDC 979252 (3aa) contains 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.
83. Ueura, K.; Satoh, T.; Miura, M. Org. Lett. 2007, 9, 1407
84. Ueura, K.; Satoh, T.; Miura, M. J. Org. Chem. 2007, 72, 5362