Highly regioselective C-N bond formation through C-H azolation of indoles promoted by iodine in aqueous media

Organic Letters

Volumn 14, Issue 23, 2012, Pages 5832-5835

  Wu, Wen Bin ^a   Huang, Jing Mei ^a  

^a SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; IODINE; PYRROLE DERIVATIVE; WATER;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

AZOLES; CATALYSIS; INDOLES; IODINE; MOLECULAR STRUCTURE; STEREOISOMERISM; WATER;

EID: 84870889259     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol302609m     Document Type: Article

References (44)

1. Sundberg, R. J. Indoles; Academic Press: San Diego, 1996.
2. Sundberg, R. J. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996; Vol. 2, p 119.
3. Gribble, G. W. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996; Vol. 2, p 207.
4. Joule, J. A. In Science of Synthesis - Houben-Weyl Methods of Molecular Transformations; Thomas, E. J., Ed.; Thieme: Stuttgart, 2000; Vol. 10, p 361.
5. Gribble, G. W. J. Chem. Soc., Perkin Trans. 1 2000, 1045
6. Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2873
7. Seregin, I. V.; Gevorgyan, V. Chem. Soc. Rev. 2007, 36, 1173
8. Bandini, M.; Eichholzer, A. Angew. Chem., Int. Ed. 2009, 48, 9608
9. Shuai, Q.; Deng, G.; Chua, Z.; Bohle, D. S.; Li, C.-J. Adv. Synth. Catal. 2010, 352, 632
10. Liu, X.-Y.; Gao, P.; Shen, Y.-W.; Liang, Y.-M. Org. Lett. 2011, 13, 4196
11. Li, Y.-X.; Ji, K.-G.; Wang, H.-X.; Ali, S.; Liang, Y.-M. J. Org. Chem. 2011, 76, 744
12. Li, Y.-X.; Wang, H.-X.; Ali, S.; Xia, X.-F.; Liang, Y.-M. Chem. Commun. 2012, 48, 2343
13. Deslandes, S.; Chassaing, S.; Delfourne, E. Tetrahedron Lett. 2010, 51, 5640
14. Deslandes, S.; Lamoral-Theys, D.; Frongia, C.; Chassaing, S.; Bruyère, C.; Lozach, O.; Meijer, L.; Ducommun, B.; Kiss, R.; Delfourne, E. Eur. J. Med. Chem. 2012, 54, 626
15. Lauria, A.; Patella, C.; Diana, P.; Barraja, P.; Montalbano, A.; Cirrincione, G.; Dattolo, G.; Almerico, A. M. Heterocycles 2003, 60, 2669
16. Lauria, A.; Patella, C.; Diana, P.; Barraja, P.; Montalbano, A.; Cirrincione, G.; Dattolo, G.; Almerico, A. M. Tetrahedron Lett. 2006, 47, 2187
17. Lauria, A.; Patella, C.; Dattolo, G.; Almerico, A. M. J. Med. Chem. 2008, 51, 2037
18. Morita, H.; Shimbo, K.; Shigemori, H.; Kobayashi, J. Bioorg. Med. Chem. Lett. 2000, 10, 469
19. Kobayashi, J.; Suzuki, H.; Shimbo, K.; Takeya, K.; Morita, H. J. Org. Chem. 2001, 66, 6626
20. Suzuki, H.; Morita, H.; Iwasaki, S.; Kobayashi, J. Tetrahedron 2003, 59, 5307
21. Suzuki, H.; Morita, H.; Shiro, M.; Kobayashi, J. Tetrahedron 2004, 60, 2489
22. Somei, M.; Tanimoto, A.; Orita, H.; Yamada, F.; Ohta, T. Heterocycles 2001, 54, 425
23. Yamada, K.; Yamada, F.; Shiraishi, T.; Tomioka, S.; Somei, M. Heterocycles 2009, 77, 971
24. Benkli, K.; Demirayak, S.; Gundogdu-Karaburun, N.; Kiraz, N.; Iscan, G.; Ucucu, U. Indian J. Chem. 2004, 43B, 174
25. Comber, M. F.; Moody, C. J. Synthesis 1992, 731
26. Harrison, J. R.; Moody, C. J. Tetrahedron Lett. 2003, 44, 5189
27. Poirier, M.; Goudreau, S.; Poulin, J.; Savoie, J.; Beaulieu, P. L. Org. Lett. 2010, 12, 2334
28. He, L.; Yang, L.; Castle, S. L. Org. Lett. 2006, 8, 1165
29. Ma, B.; Litvinov, D. N.; He, L.; Banerjee, B.; Castle, S. L. Angew. Chem., Int. Ed. 2009, 48, 6104
30. Ma, B.; Banerjee, B.; Litvinov, D. N.; He, L.; Castle, S. L. J. Am. Chem. Soc. 2010, 132, 1159
31. Feng, Y.; Chen, G. Angew. Chem., Int. Ed. 2010, 49, 958
32. Hu, W.; Zhang, F.; Xu, Z.; Liu, Q.; Cui, Y.; Jia, Y. Org. Lett. 2010, 12, 956
33. Li, C.-J. Chem. Rev. 2005, 105, 3095
34. Loh, T. P. In Science of Synthesis; Yamamoto, H., Ed.; Georg Thieme Verlag: New York, 2004; p 413.
35. Lindström, U. M. Chem. Rev. 2002, 102, 2751
36. Li, C.-J. Acc. Chem. Res. 2002, 35, 533
37. Li, C.-J. Chem. Rev. 1993, 93, 2023
38. Huang, J.; Zhou, L.; Jiang, H. Angew. Chem., Int. Ed. 2006, 45, 1945
39. Huang, J.-M.; Dong, Y. Chem. Commun. 2009, 3943
40. Huang, J.-M.; Ren, H.-R. Chem. Commun. 2010, 46, 2286
41. Huang, J.-M.; Dong, Y.; Wang, X.-X.; Luo, H.-C. Chem. Commun. 2010, 46, 1035
42. Huang, J.-M.; Wang, X.-X.; Dong, Y. Angew. Chem., Int. Ed. 2011, 50, 924
43. Huang, J.-M.; Lin, Z.-Q.; Chen, D.-S. Org. Lett. 2012, 14, 22
44. For example, see: Lengyel, I.; Epstein, I. R.; Kustin, K. Inorg. Chem. 1993, 32, 5880 and references cited therein