Multicatalytic one-pot reaction of 1-(2-alkynylphenyl)ketoximes for generation of indole derivatives

Organic Letters

Volumn 12, Issue 18, 2010, Pages 3975-3977

  Qiu, Guanyinsheng ^a   Ding, Qiuping ^a   Ren, Hui ^b   Peng, Yiyuan ^a   Wu, Jie ^b  

^a FUDAN UNIVERSITY   (China)

^b JIANGXI NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77956595417     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101487q     Document Type: Article

References (70)

1. For selected examples, see
2. Montgomery, J. Angew. Chem., Int. Ed. 2004, 43, 3890
3. Negishi, E.; Coperet, C.; Ma, S.; Liou, S. Y.; Liu, F. Chem. Rev. 1996, 96, 365
4. Tietze, L. F. Chem. Rev. 1996, 96, 115
5. Grigg, R.; Sridharan, V. J. Organomet. Chem. 1999, 576, 65
6. Miura, T.; Murakami, M. Chem. Commun. 2007, 217
7. Malacria, M. Chem. Rev. 1996, 96, 289
8. Nicolaou, K. C.; Montagnon, T.; Snyder, S. A. Chem. Commun. 2003, 551
9. Nicolaou, K. C.; Edmonds, D. J.; Bulger, P. G. Angew. Chem., Int. Ed. 2006, 45, 7134
10. Enders, D.; Grondal, C.; Huöttl, M. R. M. Angew. Chem., Int. Ed. 2007, 46, 1570
11. Tietze, L. F.; Brasche, G.; Gericke, K. Domino Reactions in Organic Synthesis; Wiley-VCH: Weinheim, Germany, 2006.
12. Chen, Z.; Yu, X.; Su, M.; Yang, X.; Wu, J. Adv. Synth. Catal. 2009, 351, 2702
13. Ding, Q.; Wang, Z.; Wu, J. J. Org. Chem. 2009, 74, 921
14. Ding, Q.; Wang, Z.; Wu, J. Tetrahedron Lett. 2009, 50, 198
15. Ding, Q.; Wu, J. Adv. Synth. Catal. 2008, 350, 1850
16. Ye, S.; Gao, K.; Wu, J. Adv. Synth. Catal. 2010, 352, 1746
17. For recent selected examples, see
18. Yu, X.; Wu, J. J. Comb. Chem. 2010, 12, 238
19. Yu, X.; Chen, Z.; Yang, X.; Wu, J. J. Comb. Chem. 2010, 12, 374
20. Chen, Z.; Yang, X.; Wu, J. Chem. Commun. 2009, 3469
21. Chen, Z.; Ding, Q.; Yu, X.; Wu, J. Adv. Synth. Catal. 2009, 351, 1692
22. Ding, Q.; He, X.; Wu, J. J. Comb. Chem. 2009, 11, 587
23. Yu, X.; Wu, J. J. Comb. Chem. 2009, 11, 895
24. Ding, Q.; Huang, X.; Wu, J. J. Comb. Chem. 2009, 11, 1047
25. For reviews, see
26. Gawly, R. E. Org. React. 1988, 35, 1 and references therein
27. Smith, M. B.; March, J. In Advanced Organic Chemistry, 5th ed.; John Wiley & Sons: New York, 2001; p 1415 and references therein.
28. Kuörti, L.; Czakó, B. Strategic Applications of Named Reactions in Organic Synthesis; Elsevier Academic Press: New York, 2005.
29. For selected examples, see
30. Boero, M.; Ikeshoji, T.; Liew, C. C.; Terakura, K.; Parrinello, M. J. Am. Chem. Soc. 2004, 126, 6280
31. De Luca, L.; Giacomelli, G.; Porcheddu, A. J. Org. Chem. 2002, 67, 6272
32. Zicmanis, A.; Katkevica, S.; Mekss, P. Catal. Commun. 2009, 10, 614
33. Pi, H. J.; Dong, J. D.; An, N.; Du, W. T.; Deng, W. P. Tetrahedron 2009, 65, 7790
34. Zhu, M. Z.; Cha, C. T.; Deng, W. P.; Shi, X. X. Tetrahedron Lett. 2006, 47, 4861
35. Hashimoto, M.; Obora, Y.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2008, 73, 2894
36. Fernandez, A. B.; Boronat, M.; Blasco, T.; Corna, A. Angew. Chem., Int. Ed. 2005, 44, 2370
37. Furuya, Y.; Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 2005, 127, 11240
38. For reviews on indole chemistry, see
39. Sundberg, R. L. Indoles; Academic: London, 1996.
40. Katritzky, A. R.; Pozharskii, A. F. Handbook of Heterocyclic Chemistry; Pergamon: Oxford, 2000; Chapter 4.
41. Joule, J. A. In Science of Synthesis (Houben-Weyl Methods of Molecular Transformations); Thomas, E. J., Ed.; Georg Thieme: Stuttgart, 2000; Vol. 10, pp 361 - 652.
42. Li, J. J.; Gribble, G. W. In Palladium in Heterocyclic Chemistry; Pergamon: Oxford, 2000; Chapter 3.
43. For other references, see: Gribble, G. W. J. Chem. Soc., Perkin Trans. 1 2000, 1045
44. Gribble, G. W. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon Press: Oxford, UK, 1996; Vol. 2, p 207.
45. Kruger, K.; Tillack, A.; Beller, M. Adv. Synth. Catal. 2008, 350, 2139
46. For selected examples, see
47. Iritani, K.; Matsubara, S.; Utimoto, K. Tetrahedron Lett. 1988, 29, 1799
48. Rudisill, D. E.; Stille, J. K. J. Org. Chem. 1989, 54, 5856
49. Saxton, J. E. Nat. Prod. Rep. 1997, 14, 559]
50. Toyota, M.; Ihara, N. Nat. Prod. Rep. 1998, 15, 327 and references therein
51. For selected recent reviews on multicatalysis, see
52. Ajamian, A.; Gleason, J. L. Angew. Chem., Int. Ed. 2004, 43, 3754
53. Lee, J. M.; Na, Y.; Han, H.; Chang, S. Chem. Soc. Rev. 2004, 33, 302
54. Wasilke, J. C.; Brey, O. S. J.; Baker, R. T.; Bazan, G. C. Chem. Rev. 2005, 105, 1001
55. Enders, D.; Grondal, C.; Huttl, M. R. Angew. Chem., Int. Ed. 2007, 46, 1570
56. Chapman, C. J.; Frost, C. G. Synthesis 2007, 1
57. Walji, A. M.; MacMillan, D. W. C. Synlett 2007, 1477
58. Wang, C.; Xi, Z. Chem. Soc. Rev. 2007, 36, 1395
59. Shao, Z.; Zhang, H. Chem. Soc. Rev. 2009, 38, 2745
60. For recent selected examples, see
61. Cernak, T. A.; Lambert, T. H. J. Am. Chem. Soc. 2009, 131, 3124 and references cited therein
62. Kelly, B. D.; Allen, J. M.; Tundel, R. E.; Lambert, T. H. Org. Lett. 2009, 11, 1381
63. Lu, L.-Q.; Cao, Y.-J.; Liu, X.-P.; An, J.; Yao, C.-J.; Ming, Z.-H.; Xiao, W.-J. J. Am. Chem. Soc. 2008, 130, 6946
64. Hu, W.; Xu, X.; Zhou, J.; Liu, W.-J.; Huang, H.; Hu, J.; Yang, L.; Gong, L.-Z. J. Am. Chem. Soc. 2008, 130, 7782
65. Ding, Q.; Wu, J. Org. Lett. 2007, 9, 4959
66. Gao, K.; Wu, J. J. Org. Chem. 2007, 72, 8611
67. Ye, S.; Wu, J. Tetrahedron Lett. 2009, 50, 6273
68. Yu, X.; Yang, X.; Wu, J. Org. Biomol. Chem. 2009, 7, 4526
69. Takao, S.; Kondo, Y.; Miura, N.; Hayashi, K.; Yamanaka, H. Heterocycles 1986, 24, 2311
70. Tang, S.; Xie, Y. X.; Li, J. H.; Wang, N. X. Synthesis 2007, 1841