Synthesis of Indolo[1,2- a ][1,8]naphthyridines by Rhodium(III)-Catalyzed Dehydrogenative Coupling via Rollover Cyclometalation

Organic Letters

Volumn 17, Issue 12, 2015, Pages 3130-3133

  Morioka, Ryosuke ^a   Nobushige, Kazunori ^a   Satoh, Tetsuya ^a,b,c   Hirano, Koji ^a   Miura, Masahiro ^a  

^a OSAKA UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^c Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; INDOLE DERIVATIVE; NAPHTHYRIDINE DERIVATIVE; RHODIUM;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; FLUORESCENCE; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; FLUORESCENCE; HETEROCYCLIC COMPOUNDS; INDOLES; MOLECULAR STRUCTURE; NAPHTHYRIDINES; RHODIUM; STEREOISOMERISM;

EID: 84934978388     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b01452     Document Type: Article

References (60)

1. Baczewski, P.; Bodzioch, A.; Różycka-Sokoowska, E.; Marciniak, B.; Uznański, P. Chem.-Eur. J. 2010, 16, 2392
2. Palayangoda, S. S.; Cai, X.; Adhikari, R. M.; Neckers, D. C. Org. Lett. 2008, 10, 281
3. Li, Y.; Wu, Y.; Gardner, S.; Ong, B. S. Adv. Mater. 2005, 17, 849
4. Hu, N.-X.; Xie, S.; Popovic, Z.; Ong, B.; HorSuning Wang, A.-M. J. Am. Chem. Soc. 1999, 121, 5097
5. Schmidt, A. W.; Reddy, K. R.; Knölker, H.-J. Chem. Rev. 2012, 112, 3193
6. Knölker, H.-J.; Reddy, K. R. Chem. Rev. 2002, 102, 4303
7. Song, G.; Li, X. Acc. Chem. Res. 2015, 48, 1007
8. Miura, M.; Satoh, T.; Hirano, K. Bull. Chem. Soc. Jpn. 2014, 87, 751
9. Jin, T.; Zhao, J.; Asao, N.; Yamamoto, Y. Chem.-Eur. J. 2014, 20, 3554
10. De Sarkar, S.; Liu, W.; Kozhushkov, S. I.; Ackermann, L. Adv. Synth. Catal. 2014, 356, 1461
11. Kuhl, N.; Schröder, N.; Glorius, F. Adv. Synth. Catal. 2014, 356, 1443
12. Shi, G.; Zhang, Y. Adv. Synth. Catal. 2014, 356, 1419
13. Bonin, H.; Sauthier, M.; Felpin, F.-X. Adv. Synth. Catal. 2014, 356, 645
14. Engle, K. M.; Yu, J.-Q. J. Org. Chem. 2013, 78, 8927
15. Wencel-Delord, J.; Glorius, F. Nat. Chem. 2013, 5, 369
16. Colby, D. A.; Tsai, A. S.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2012, 45, 814
17. Engle, K. M.; Mei, T.-S.; Wasa, M.; Yu, J.-Q. Acc. Chem. Res. 2012, 45, 788
18. Mitchell, E. A.; Peschiulli, A.; Lefevre, N.; Meerpoel, L.; Maes, B. U. W. Chem.-Eur. J. 2012, 18, 10092
19. Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev. 2011, 40, 5068
20. Wencel-Delord, J.; Droge, T.; Liu, F.; Glorius, F. Chem. Soc. Rev. 2011, 40, 4740
21. Kuninobu, Y.; Takai, K. Chem. Rev. 2011, 111, 1938
22. Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111, 1780
23. Ackermann, L. Chem. Rev. 2011, 111, 1315
24. Lapointe, D.; Fagnou, K. Chem. Lett. 2010, 39, 1118
25. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
26. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624
27. Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Commun. 2010, 46, 677
28. Satoh, T.; Miura, M. Chem.-Eur. J. 2010, 16, 11212
29. Satoh, T.; Miura, M. Synthesis 2010, 3395
30. Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094
31. Daugulis, O.; Do, H.-Q.; Shabashov, D. Acc. Chem. Res. 2009, 42, 1074
32. McGlacken, G. P.; Bateman, L. M. Chem. Soc. Rev. 2009, 38, 2447
33. Li, C.-J. Acc. Chem. Res. 2009, 42, 335
34. Kakiuchi, F.; Kochi, T. Synthesis 2008, 3013
35. Ferreira, E. M.; Zhang, H.; Stoltz, B. M. Tetrahedron 2008, 64, 5987
36. Park, Y. J.; Park, J.-W.; Jun, C.-H. Acc. Chem. Res. 2008, 41, 222
37. Beccalli, E. M.; Broggini, G.; Martinelli, M.; Sottocornola, S. Chem. Rev. 2007, 107, 5318
38. Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174
39. Godula, K.; Sames, D. Science 2006, 312, 67
40. Kakiuchi, F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077
41. Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1698
42. Li, L.; Brennessei, W. W.; Jones, W. D. J. Am. Chem. Soc. 2008, 130, 12414
43. Luo, C.-Z.; Gandeepan, P.; Jayakumar, J.; Parthasarathy, K.; Chang, Y.-W.; Cheng, C.-H. Chem.-Eur. J. 2013, 19, 14181
44. Zhang, G.; Yang, L.; Wang, Y.; Xie, Y.; Huang, H. J. Am. Chem. Soc. 2013, 135, 8850
45. Butschke, B.; Schwarz, H. Chem. Sci. 2012, 3, 308
46. Shibata, T.; Takayasu, S.; Yuzawa, S.; Otani, T. Org. Lett. 2012, 14, 5106
47. Kwak, J.; Ohk, Y.; Jung, Y.; Chang, S. J. Am. Chem. Soc. 2012, 134, 17778
48. Katagiri, T.; Mukai, T.; Satoh, T.; Hirano, K.; Miura, M. Chem. Lett. 2009, 38, 118
49. Qi, Z.; Yu, S.; Li, X. J. Org. Chem. 2015, 80, 3471
50. Huang, J.-R.; Zhang, Q.-R.; Qu, C.-H.; Sun, X.-H.; Dong, L.; Chen, Y.-C. Org. Lett. 2013, 15, 1878
51. Huang, J.-R.; Dong, L.; Han, B.; Peng, C.; Chen, Y.-C. Chem.-Eur. J. 2012, 18, 8896
52. Umeda, N.; Hirano, K.; Satoh, T.; Shibata, N.; Sato, H.; Miura, M. J. Org. Chem. 2011, 76, 13
53. Iitsuka, T.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2015, 80, 2804
54. Itoh, M.; Hirano, K.; Satoh, T.; Shibata, Y.; Tanaka, K.; Miura, M. J. Org. Chem. 2013, 78, 1365
55. Mochida, S.; Umeda, N.; Hirano, K.; Satoh, T.; Miura, M. Chem. Lett. 2010, 39, 744
56. Morimoto, K.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2010, 12, 2068
57. Tateno, K.; Ogawa, R.; Sakamoto, R.; Tsuchiya, M.; Otani, T.; Saito, T. Org. Lett. 2014, 16, 3212
58. Otani, T.; Saito, T.; Sakamoto, R.; Osada, H.; Hirahara, A.; Furukawa, N.; Kutsumura, N.; Matsuo, T.; Tamao, K. Chem. Commun. 2013, 49, 6206
59. Liang, L.; Fu, S.; Lin, D.; Zhang, X.-Q.; Deng, Y.; Jiang, H.; Zeng, W. J. Org. Chem. 2014, 79, 9472
60. Schipper, D. J.; Hutchinson, M.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 6910