Palladium and copper cocatalyzed tandem N-H/C-H bond functionalization: Synthesis of CF 3-containing indolo- and pyrrolo[2,1-a ]isoquinolines

Journal of Organic Chemistry

Volumn 77, Issue 6, 2012, Pages 2850-2856

  Sun, Lei Lei ^a   Liao, Zhi Yong ^a   Tang, Ri Yuan ^a   Deng, Chen Liang ^a   Zhang, Xing Guo ^a  

^a WENZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

FUNCTIONALIZATION REACTIONS; FUNCTIONALIZATIONS; GOOD YIELD; ISOQUINOLINES;

BENZENE;

COPPER;

BROMOBENZENE; COPPER; FLUORINE DERIVATIVE; INDOLO[2,1 A]ISOQUINOLINE DERIVATIVE; ISOQUINOLINE DERIVATIVE; METHYL GROUP; PALLADIUM; PYRROLO[2,1 A]ISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CYCLIZATION; REACTION ANALYSIS;

BROMOBENZENES; CATALYSIS; COPPER; INDOLES; ISOQUINOLINES; MOLECULAR STRUCTURE; PALLADIUM; PYRROLES;

EID: 84863387863     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo3000404     Document Type: Article

References (60)

1. Anderson, W. K.; Heider, A. R.; Raju, N.; Yucht, J. A. J. Med. Chem. 1988, 31, 2097
2. Goldbrunner, M.; Loidl, G.; Polossek, T.; Mannschreck, A.; von Angerer, E. J. Med. Chem. 1997, 40, 3524
3. Ambros, R.; von Angerer, S.; Wiegrebe, W. Arch. Pharm. 1988, 321, 481
4. Ambros, R.; von Angerer, S.; Wiegrebe, W. Arch. Pharm. 1988, 321, 743
5. Watson, M. D.; Fechtenkötter, A.; Müllen, K. Chem. Rev. 2001, 101, 1267
6. Ahmed, E.; Briseno, A. L.; Xia, Y.; Jenekhe, S. A. J. Am. Chem. Soc. 2008, 130, 1118
7. Boden, N.; Bissell, R.; Clements, J.; Movaghar, B. Liq. Cryst. Today 1996, 6, 1
8. Chandrasekhar, S. Liq. Cryst. 1993, 14, 3
9. Ewing, J.; Hughes, G. K.; Ritchie, E.; Taylor, W. C. Nature 1952, 169, 618
10. Moskowitz, H.; Leboeuf, M.; Care, A.; von Angerer, A. Can. J. Chem. 1989, 67, 947
11. Morimoto, K.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2010, 12, 2068
12. Lötter, A. N. C.; Pathak, R.; Sello, T. S.; Fernandes, M. A.; van Otterlo, W. A. L.; de Koning, C. B. Tetrahedron 2007, 63, 2263
13. de Koning, C. B.; Michael, J. P.; Pathak, R.; van Otterlo, W. A. L. Tetrahedron Lett. 2004, 45, 1117
14. Mamane, V.; Hannen, P.; Fürstner, A. Chem.-Eur. J. 2004, 10, 4556
15. Waldmann, H.; Eberhardt, L.; Wittsteinab, K.; Kumar, K. Chem. Commun. 2010, 46, 4622
16. Menes-Arzate, M.; Martänez, R.; Cruz-Almanza, R.; Muchowski, J. M.; Osornio, Y. M.; Miranda, L. D. J. Org. Chem. 2004, 69, 4001
17. Reboredo, F. J.; Treus, M.; Estévez, J. C.; Castedo, L.; Estévez, R. J. Synlett 2003, 1603
18. Ackermann, L.; Wang, L.; Lygin, A. V. Chem. Sci. 2012, 3, 177
19. Ambros, R.; Schneider, M. R.; von Angerer, S. J. Med. Chem. 1990, 33, 153
20. Elwan, N. M.; Abdelhadi, H. A.; Abdallah, T. A.; Hassaneen, H. M. Tetrahedron 1996, 52, 3451
21. Zhao, B.-X.; Yu, Y.; Eguchi, S. Tetrahedron 1996, 52, 12049
22. Katritzky, A. R.; Qiu, G.; Yang, B.; He, H.-Y. J. Org. Chem. 1999, 64, 7618
23. Orito, K.; Uchiito, S.; Satoh, Y.; Tatsuzawa, T.; Harada, R.; Takuda, M. Org. Lett. 2000, 2, 307
24. Barun, O.; Chakrabarti, S.; Ila, H.; Junjappa, H. J. Org. Chem. 2001, 66, 4457
25. Orito, K.; Harada, R.; Uchiito, S.; Tokuda, M. Org. Lett. 2000, 2, 1799
26. Vincze, Z.; Beatrix Bíró, A.; Csékei, M.; Timári, G.; Kotschy, A. Synthesis 2006, 1375
27. Pivsa-Art, S.; Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Bull. Chem. Soc. Jpn. 1998, 71, 467
28. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
29. Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174
30. Daugulis, O.; Do, H.-Q.; Shabashov, D. Acc. Chem. Res. 2009, 42, 1074
31. Nolan, S. P. Acc. Chem. Res. 2011, 44, 91
32. Lewis, J. C.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2008, 41, 1013
33. Engle, K. M.; Mei, T.-S.; Wang, X.; Yu, J.-Q. Angew. Chem., Int. Ed. 2011, 50, 1478
34. Werner, H. Angew. Chem., Int. Ed. 2010, 49, 4714
35. Thansandote, P.; Lautens, M. Chem.-Eur. J. 2009, 15, 5874
36. Ackermann, L.; Vicente, R.; Kapdi, A. R. Angew. Chem., Int. Ed. 2009, 48, 9792
37. Sun, C.-L.; Li, B.-J.; Shi., Z.-J. Chem. Commun. 2010, 46, 677
38. Kantak, A. A.; Potavathri, S.; Barham, R. A.; Romano, K. M.; DeBoef, B. J. Am. Chem. Soc. 2011, 133, 19960
39. Ruck, R. T.; Huffman, M. A.; Kim, M. M.; Shevlin, M.; Kandur, W. V.; Davies, I. W. Angew. Chem., Int. Ed. 2008, 47, 4711
40. Zhang, J.; Zhu, D.; Yu, C.; Wan, C.; Wang, Z. Org. Lett. 2010, 12, 2841
41. Serna, S.; Tellitu, I.; Domínguez, E.; Moreno, I.; SanMartín, R. Org. Lett. 2005, 7, 3073
42. Pastine, S. J.; Sames, D. Org. Lett. 2005, 7, 5429
43. Xu, R.; Wan, J.-P.; Mao, H.; Pan, Y. J. Am. Chem. Soc. 2010, 132, 15531
44. Bedford, R. B.; Betham, M. J. Org. Chem. 2006, 71, 9403
45. Ackermann, L.; Althammer, A.; Mayer, P. Synthesis 2009, 3493
46. Bedford, R. B.; Betham, M.; Charmant, J. P. H; Weeks, A. L. Tetrahedron 2008, 64, 6038
47. Verma, A. K.; Kesharwani, T.; Singh, J.; Tandon, V.; Larock, R. C. Angew. Chem., Int. Ed. 2009, 48, 1138
48. Liao, Q.; Zhang, L.; Li, S.; Xi, C. Org. Lett. 2011, 13, 228
49. Schlosser, M. Angew. Chem., Int. Ed. 2005, 44, 214
50. Muller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881
51. Purser, S.; Moore; P., R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320
52. Hagmann, W. K. J. Med. Chem. 2008, 51, 4359
53. Welch, J. T. Tetrahedron 1987, 43, 3123
54. Chen, M.-W.; Zhang, X.-G.; Zhong, P.; Hu, M.-L. Synthesis 2009, 1431
55. Dong, S.-X.; Zhang, X.-G.; Liu, Q.; Tang, R.-Y.; Zhong, P.; Li, J.-H. Synthesis 2010, 1521
56. Li, C.-L.; Zhang, X.-G.; Tang, R.-Y.; Zhong, P.; Li, J.-H. J. Org. Chem. 2010, 75, 7037
57. Fujita, M.; Hiyama, T. Bull. Chem. Soc. Jpn. 1987, 60, 4377
58. Korotchenko, V. N.; Shastin, A. V.; Nenajdenko, V. G.; Balenkova, E. S. Tetrahedron 2001, 57, 7519
59. Chen, M.-W.; Zhang, X.-G.; Zhong, P.; Hu, M.-L. Synth. Commun. 2009, 39, 756
60. Lane, B. S.; Brown, M. A.; Sames, D. J. Am. Chem. Soc. 2005, 127, 8050