Rh(III)-catalyzed oxidative Annulation of 2-phenylimidazo[1,2- a ]pyridines with alkynes: Mono versus double C-H activation

Journal of Organic Chemistry

Volumn 80, Issue 7, 2015, Pages 3471-3479

  Qi, Zisong ^a   Yu, Songjie ^a   Li, Xingwei ^a  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ANALYSIS; CATALYSIS; HYDROCARBONS; OXIDANTS; PYRIDINE; RHODIUM;

BENZENE RING; C-H ACTIVATION; C-N COUPLING; CONDITION CONTROL; OXIDATIVE ANNULATION; OXIDATIVE COUPLINGS;

CHEMICAL ACTIVATION;

ALKYNE; NITROGEN; PHENYLIMIDAZO[1,2 A]PYRIDINE DERIVATIVE; PYRIDINE DERIVATIVE; RHODIUM; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CATALYSIS; CHELATION; OXIDATIVE COUPLING; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 84926505025     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b00059     Document Type: Article

References (77)

1. Allard, S.; Forster, M.; Souharce, B.; Thiem, H.; Scherf, U. Angew. Chem., Int. Ed. 2008, 47, 4070
2. Facchetti, A. Chem. Mater. 2011, 23, 733
3. Wang, C.; Dong, H.; Hu, W.; Liu, Y.; Zhu, D. Chem. Rev. 2012, 112, 2208
4. Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731
5. Ackermann, L.; Vicente, R.; Kapdi, A. R. Angew. Chem., Int. Ed. 2009, 48, 9792
6. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624
7. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
8. Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Rev. 2010, 111, 1293
9. Ackermann, L. Chem. Rev. 2011, 111, 1315
10. Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev. 2011, 40, 5068
11. Wencel-Delord, J.; Droge, T.; Liu, F.; Glorius, F. Chem. Soc. Rev. 2011, 40, 4740
12. Wendlandt, A. E.; Suess, A. M.; Stahl, S. S. Angew. Chem., Int. Ed. 2011, 50, 11062
13. Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215
14. Arockiam, P. B.; Bruneau, C.; Dixneuf, P. H. Chem. Rev. 2012, 112, 5879
15. Engle, K. M.; Mei, T.-S.; Wasa, M.; Yu, J.-Q. Acc. Chem. Res. 2012, 45, 788
16. Kuhl, N.; Hopkinson, M. N.; Wencel-Delord, J.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 10236
17. White, M. C. Science 2012, 335, 807
18. Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem., Int. Ed. 2012, 51, 8960
19. Shang, X.; Liu, Z.-Q. Chem. Soc. Rev. 2013, 42, 3253
20. Yan, G.; Wu, X.; Yang, M. Org. Biomol. Chem. 2013, 11, 5558
21. Ackermann, L. Acc. Chem. Res. 2014, 47, 281
22. Zhang, M.; Zhang, Y.; Jie, X.; Zhao, H.; Li, G.; Su, W. Org. Chem. Front. 2014, 1, 843
23. Segawa, Y.; Maekawa, T.; Itami, K. Angew. Chem., Int. Ed. 2015, 54, 66
24. Gutekunst, W. R.; Baran, P. S. Chem. Soc. Rev. 2011, 40, 1976
25. McMurray, L.; OHara, F.; Gaunt, M. J. Chem. Soc. Rev. 2011, 40, 1885
26. Chen, D. Y. K.; Youn, S. W. Chem.-Eur. J. 2012, 18, 9452
27. Colby, D. A.; Tsai, A. S.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2011, 45, 814
28. Song, G.; Wang, F.; Li, X. Chem. Soc. Rev. 2012, 41, 3651
29. Kuhl, N.; Schröder, N.; Glorius, F. Adv. Synth. Catal. 2014, 356, 1443
30. Patureau, F. W.; Besset, T.; Fröhlich, R.; Glorius, F. Aldrichim. Acta 2012, 45, 31
31. Satoh, T.; Miura, M. Chem.-Eur. J. 2010, 16, 11212
32. Chen, J.; Song, G.; Pan, C.-L.; Li, X. Org. Lett. 2010, 12, 5426
33. Morimoto, K.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2011, 76, 9548
34. Patureau, F. W.; Besset, T.; Kuhl, N.; Glorius, F. J. Am. Chem. Soc. 2011, 133, 2154
35. Pham, M. V.; Ye, B.; Cramer, N. Angew. Chem., Int. Ed. 2012, 51, 10610
36. Wang, D.; Wang, F.; Song, G.; Li, X. Angew. Chem., Int. Ed. 2012, 51, 12348
37. Chen, Y.; Wang, F.; Zhen, W.; Li, X. Adv. Synth. Catal. 2013, 355, 353
38. Park, S.; Seo, B.; Shin, S.; Son, J. Y.; Lee, P. H. Chem. Commun. 2013, 49, 8671
39. Seo, J.; Park, Y.; Jeon, I.; Ryu, T.; Park, S.; Lee, P. H. Org. Lett. 2013, 15, 3358
40. Unoh, Y.; Hashimoto, Y.; Takeda, D.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2013, 15, 3258
41. Wang, C.; Sun, H.; Fang, Y.; Huang, Y. Angew. Chem., Int. Ed. 2013, 52, 5795
42. Itoh, M.; Shimizu, M.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2013, 78, 11427
43. Burns, D. J.; Lam, H. W. Angew. Chem., Int. Ed. 2014, 53, 9931
44. Seoane, A.; Casanova, N.; Quinones, N.; Mascarenas, J. L.; Gulias, M. J. Am. Chem. Soc. 2014, 136, 7607
45. Seoane, A.; Casanova, N.; Quiñones, N.; Mascareñas, J. L.; Gulías, M. J. Am. Chem. Soc. 2014, 136, 834
46. Zhang, X.; Li, Y.; Shi, H.; Zhang, L.; Zhang, S.; Xu, X.; Liu, Q. Chem. Commun. 2014, 50, 7306
47. Qi, Z.; Wang, M.; Li, X. Chem. Commun. 2014, 50, 9776
48. Kujawa, S.; Best, D.; Burns, D. J.; Lam, H. W. Chem.-Eur. J. 2014, 20, 8599
49. Chen, Y.; Wang, D.; Duan, P.; Ben, R.; Dai, L.; Shao, X.; Hong, M.; Zhao, J.; Huang, Y. Nat. Commun. 2014, 5, 4610
50. Sun, H.; Wang, C.; Yang, Y.-F.; Chen, P.; Wu, Y.-D.; Zhang, X.; Huang, Y. J. Org. Chem. 2014, 79, 11863
51. Umeda, N.; Tsurugi, H.; Satoh, T.; Miura, M. Angew. Chem., Int. Ed. 2008, 47, 4019
52. Fukutani, T.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2011, 76, 2867
53. Morimoto, K.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2010, 12, 2068
54. Iitsuka, T.; Hirano, K.; Satoh, T.; Miura, M. Chem.-Eur. J. 2014, 20, 385
55. Pham, M. V.; Cramer, N. Angew. Chem., Int. Ed. 2014, 53, 3484
56. Huang, J.-R.; Zhang, Q.-R.; Qu, C.-H.; Sun, X.-H.; Dong, L.; Chen, Y.-C. Org. Lett. 2013, 15, 1878
57. Huang, J.-R.; Dong, L.; Han, B.; Peng, C.; Chen, Y.-C. Chem.-Eur. J. 2012, 18, 8896
58. Tan, X.; Liu, B.; Li, X.; Li, B.; Xu, S.; Song, H.; Wang, B. J. Am. Chem. Soc. 2012, 134, 16163
59. Zheng, L.; Hua, R. J. Org. Chem. 2014, 79, 3930
60. Jayakumar, J.; Parthasarathy, K.; Chen, Y. H.; Lee, T. H.; Chuang, S. C.; Cheng, C. H. Angew. Chem., Int. Ed. 2014, 53, 9889
61. Zhang, L.; Zheng, L.; Guo, B.; Hua, R. J. Org. Chem. 2014, 79, 11541
62. Song, G.; Chen, D.; Pan, C.-L.; Crabtree, R. H.; Li, X. J. Org. Chem. 2010, 75, 7487
63. Song, G.; Gong, X.; Li, X. J. Org. Chem. 2011, 76, 7583
64. Qi, Z.; Li, X. Angew. Chem., Int. Ed. 2013, 52, 8995
65. Yu, S.; Li, X. Org. Lett. 2014, 16, 1220
66. Kwak, J.; Ohk, Y.; Jung, Y.; Chang, S. J. Am. Chem. Soc. 2012, 134, 17778
67. Zucca, A.; Cinellu, M. A.; Pinna, M. V.; Stoccoro, S.; Minghetti, G.; Manassero, M.; Sansoni, M. Organometallics 2000, 19, 4295
68. Minghetti, G.; Stoccoro, S.; Cinellu, M. A.; Soro, B.; Zucca, A. Organometallics 2003, 22, 4770
69. Muralirajan, K.; Cheng, C.-H. Chem.-Eur. J. 2013, 19, 6198
70. Jayakumar, J.; Parthasarathy, K.; Cheng, C.-H. Angew. Chem., Int. Ed. 2012, 51, 197
71. Luo, C.-Z.; Gandeepan, P.; Jayakumar, J.; Parthasarathy, K.; Chang, Y.-W.; Cheng, C.-H. Chem.-Eur. J. 2013, 19, 14181
72. Luo, C.-Z.; Gandeepan, P.; Cheng, C.-H. Chem. Commun. 2013, 49, 8528
73. Zhao, D.; Wu, Q.; Huang, X.; Song, F.; Lv, T.; You, J. Chem.-Eur. J. 2013, 19, 6239
74. Zhang, G.; Yang, L.; Wang, Y.; Xie, Y.; Huang, H. J. Am. Chem. Soc. 2013, 135, 8850
75. Mio, M. J.; Kopel, L. C.; Braun, J. B.; Gadzikwa, T. L.; Hull, K. L.; Brisbois, R. G.; Markworth, C. J.; Grieco, P. A. Org. Lett. 2002, 4, 3199
76. Aginagalde, M.; Vara, Y.; Arrieta, A.; Zangi, R.; Cebolla, V. L.; Delgado-Camón, A.; Cossío, F. P. J. Org. Chem. 2009, 75, 2776
77. Fujita, K.-i.; Takahashi, Y.; Owaki, M.; Yamamoto, K.; Yamaguchi, R. Org. Lett. 2004, 6, 2785