Gold-catalyzed deacylative cycloisomerization reactions of 3-acylindole/ynes: A new approach for carbazole synthesis

Organic Letters

Volumn 13, Issue 15, 2011, Pages 3786-3789

  Wang, Lu ^a   Li, Guijie ^a   Liu, Yuanhong ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79961076743     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2012154     Document Type: Article

References (57)

1. For recent reviews on gold-catalyzed reactions, see: Hashmi, A. S. K.; Hutchings, G. J. Angew. Chem., Int. Ed. 2006, 45, 7896
2. Gorin, D. J.; Toste, F. D. Nature 2007, 446, 395
3. Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180
4. Fürstner, A.; Davies, P. W. Angew. Chem., Int. Ed. 2007, 46, 3410
5. Jiménez-Núñez, E.; Echavarren, A. M. Chem. Commun. 2007, 333
6. Lipshutz, B. H.; Yamamoto, Y. Chem. Rev. 2008, 108, 2793
7. Jiménez-Núñez, E.; Echavarren, A. M. Chem. Rev. 2008, 108, 3326
8. Gorin, D. J.; Sherry, B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351
9. Arcadi, A. Chem. Rev. 2008, 108, 3266
10. Patil, N. T.; Yamamoto, Y. Chem. Rev. 2008, 108, 3395
11. Li, Z.; Brouwer, C.; He, C. Chem. Rev. 2008, 108, 3239
12. Muzart, J. Tetrahedron 2008, 64, 5815
13. Shen, H. C. Tetrahedron 2008, 64, 3885
14. Shapiro, N.; Toste, D. Synlett 2010, 675
15. Corma, A.; Leyva-Pérez, A.; Sabater, M. J. Chem. Rev. 2011, 111, 1657
16. Bandini, M. Chem. Soc. Rev. 2011, 40, 1358
17. Ferrer, C.; Echavarren, A. M. Angew. Chem., Int. Ed. 2006, 45, 1105
18. Ferrer, C.; Amijs, C. H. M.; Echavarren, A. M. Chem.-Eur. J. 2007, 13, 1358
19. Ferrer, C.; Escribano-Cuesta, A.; Echavarren, A. M. Tetrahedron 2009, 65, 9015
20. England, D. B.; Padwa, A. Org. Lett. 2008, 10, 3631
21. Verniest, G.; England, D.; De Kimpe, N.; Padwa, A. Tetrahedron 2010, 66, 1496
22. Liu, Y.; Xu, W.; Wang, X. Org. Lett. 2010, 7, 1448
23. Sanz, R.; Miguel, D.; Rodríguez, F. Angew. Chem., Int. Ed. 2008, 47, 7354
24. Zhang, G.; Huang, X.; Li, G.; Zhang, L. J. Am. Chem. Soc. 2008, 130, 1814
25. Zhang, L. J. Am. Chem. Soc. 2005, 127, 16804
26. Lu, Y.; Du, X.; Jia, X.; Liu, Y. Adv. Synth. Catal. 2009, 351, 1517
27. Li, G.; Liu, Y. J. Org. Chem. 2010, 75, 3526
28. For hydroxy-group induced fragmentation, see: Grob, C. A.; Schiess, P. W. Angew. Chem., Int. Ed. 1967, 6, 1
29. Paquette, L. A.; Yang, J.; Long, Y. O. J. Am. Chem. Soc. 2002, 124, 6542
30. For transition-metal-catalyzed synthesis of carbazoles, see: Hans-Knölker, J.; Reddy, K. R. Chem. Rev. 2002, 102, 4303
31. Liu, Z.; Larock, R. C. Org. Lett. 2004, 6, 3739
32. Cai, X.; Snieckus, V. Org. Lett. 2004, 6, 2293
33. Kuwahara, A.; Nakano, K.; Nozaki, K. J. Org. Chem. 2005, 70, 413
34. Zhao, J.; Larock, R. C. Org. Lett. 2005, 7, 701
35. Tsang, W. C. P.; Zheng, N.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 14560
36. Kong, A.; Han, X.; Lu, X. Org. Lett. 2006, 8, 1339
37. Jean, D. J., St. Jr.; Poon, S. F.; Schwarzbach, J. L. Org. Lett. 2007, 9, 4897
38. Liégault, B.; Lee, D.; Huestis, M. P.; Stuart, D. R.; Fagnou, K. J. Org. Chem. 2008, 73, 5022
39. Jordan-Hore, J. A.; Carin, C. C.; Gulias, M.; Beck, E. M.; Gaunt, M. J. J. Am. Chem. Soc. 2008, 130, 16184
40. Tsang, W. C. P.; Munday, R. H.; Brasche, G.; Zheng, N.; Buchwald, S. L. J. Org. Chem. 2008, 73, 7603
41. Ueno, K.; Kitawaki, T.; Chida, N. Org. Lett. 2008, 10, 1999
42. Stokes, B. J.; Jovanović, B.; Dong, H.; Richert, K. J.; Riell, R. D.; Driver, T. G. J. Org. Chem. 2009, 74, 3225
43. Kong, W.; Fu, C.; Ma, S. Chem. Commun. 2009, 4572
44. Hirano, K.; Inaba, Y.; Takahashi, N.; Shimano, M.; Oishi, S.; Fujii, N.; Ohno, H. J. Org. Chem. 2011, 76, 1212 For recent paper on gold-catalyzed cyclization of 2-(enynyl)indoles to carbazoles, see: Praveen, C.; Perumal, P. T. Synlett 2011, 521
45. For carbonyl group-induced fragmentation reaction under the reductive conditions, see: Molander, G. A.; Le Huerou, Y.; Brown, G. A. J. Org. Chem. 2001, 66, 4511
46. Prantz, K.; Mulzer, J. Chem.-Eur. J. 2010, 16, 485 For reviews, see: Prantz, K.; Mulzer, J. Chem. Rev. 2010, 110, 3741
47. For lithiation of 2-alkylindoles by lithium carbamate protection-activation, see: Katritzky, A. R.; Akutagawa, K. J. Am. Chem. Soc. 1986, 108, 6808 For C-3 carboxylate induced lateral lithiations of 2-alkyl derivatives, see: Vedejs, E.; Mullins, M. J.; Renga, J. M.; Singer, S. P. Tetrahedron Lett. 1978, 19, 519 For review on lateral lithiation reactions promoted by heteroatomic substituents, see: Clark, R. D.; Jahangir, A. Org. React. 1995, 47, 1-314
48. Knölker, H.-J.; Reddy, K. R. Chem. Rev. 2002, 102, 4303
49. Meragelman, K. M.; McKee, T. C.; Boyd, M. R. J. Nat. Prod. 2000, 63, 427
50. For the generation of acylium ions by fragmentation of the amide bond, see: Li, G.; Huang, X.; Zhang, L. Angew. Chem., Int. Ed. 2008, 47, 346
51. Peng, Y.; Yu, M.; Zhang, L. Org. Lett. 2008, 10, 5187
52. Knölker, H.-J. Top. Curr. Chem. 2005, 244, 115
53. Chakraborty, D. P.; Roy, S. In Progress in the Chemistry of Organic Natural Products; Herz, W.; Kirby, G. W.; Steglich, W.; Tamm, C., Eds.; Springer-Verlag: New York, 1991; Vol. 57, pp 72-152.
54. Zhang, Y.; Wada, T.; Sasabe, H. J. Mater. Chem. 1998, 8, 809
55. Grazulevicius, J. V.; Strohriegl, P.; Pielichowski, J.; Pielichowski, K. Prog. Polym. Sci. 2003, 28, 1297
56. Thomas, K. R. J.; Lin, J. T.; Tao, Y.-T.; Ko, C.-W. J. Am. Chem. Soc. 2001, 123, 9404
57. Díaz, J. L.; Dobarro, A.; Villacampa, B.; Velasco, D. Chem. Mater. 2001, 13, 2528