The benzyne Fischer-indole reaction

Organic Letters

Volumn 13, Issue 14, 2011, Pages 3667-3669

  McAusland, Donald ^a   Seo, Sangwon ^a   Pintori, Didier G ^a   Finlayson, Jonathan ^b   Greaney, Michael F ^a  

^a UNIVERSITY OF EDINBURGH   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; BENZYNE; HYDRAZONE DERIVATIVE; INDOLE DERIVATIVE; N TOSYLINDOLE; N-TOSYLINDOLE; TOLUENESULFONIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLIZATION; SYNTHESIS;

BENZENE DERIVATIVES; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; HYDRAZONES; INDOLES; MOLECULAR STRUCTURE; TOSYL COMPOUNDS;

EID: 79960187080     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol201413r     Document Type: Article

References (30)

1. Fischer, E.; Jourdan, F. Chem. Ber. 1883, 16, 2241
2. Fischer, E.; Hess, O. Chem. Ber. 1884, 17, 559
3. Reviews: Robinson, B. The Fischer Indole Synthesis; J. Wiley & Sons: New York, NY, 1982.
4. Hughes, D. L. Org. Prep. Proced. Int. 1993, 25, 609
5. Humphrey, G. R; Kuethe, J. T. Chem. Rev. 2006, 106, 2875
6. Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251
7. Hoffman, R. W. Dehydrobenzenes and Cycloalkynes; Academic Press, NY, 1967.
8. Selected recent examples: Hwu, J. R.; Hsu, Y. C. Chem.-Eur. J. 2011, 17, 4727
9. Truong, T.; Daugulis, O. J. Am. Chem. Soc. 2011, 133, 4243
10. Bronner, S. M.; Goetz, A. E.; Garg, N. K. J. Am. Chem. Soc. 2011, 133, 3832
11. Laczkowski, K. Z.; Garcia, D.; Pena, D.; Cobas, A.; Perez, D.; Guitian, E. Org. Lett. 2011, 13, 960
12. Biju, A. T.; Glorius, F. Angew. Chem., Int. Ed. 2010, 49, 9761
13. Kirkham, J. D.; Delaney, P. M.; Ellames, G. J.; Row, E. C.; Harrity, J. P. A. Chem. Commun. 2010, 46, 5154
14. Dubrovskiy, A. V.; Larock, R. C. Org. Lett. 2010, 12, 3117
15. Yoshida, H.; Ohshita, J.; Kunai, A. Bull. Chem. Soc. Jpn. 2010, 83, 199
16. Recent examples: Rogness, D. C.; Larock, R. C. J. Org. Chem. 2011, 76, 4980
17. Okuma, K.; Matsunaga, N.; Nagahora, N.; Shioji, K.; Yokomori, Y. Chem. Commun. 2011, 47, 5822
18. Smith, A. B., III; Kim, W.-S. Proc. Natl. Acad. Sci. U.S.A. 2011, 108, 6787
19. Okano, K.; Fujiwara, H.; Noji, T.; Fukuyama, T.; Tokuyama, H. Angew. Chem., Int. Ed. 2010, 49, 5925
20. Hong, D.; Chen, Z.; Lin, X.; Wang, Y. Org. Lett. 2010, 12, 4608
21. Wu, C.; Fang, Y.; Larock, R. C.; Shi, F. Org. Lett. 2010, 12, 2234
22. Pintori, D. G.; Greaney, M. F. Org. Lett. 2010, 12, 168
23. Jeganmohan, M.; Bhuvaneswari, S.; Cheng, C.-H. Chem.-Asian J. 2009, 5, 153
24. Cano, R.; Ramon, D. J.; Yus, M. J. Org. Chem. 2010, 76, 654
25. Cant, A. A.; Bertrand, G. H. V.; Henderson, J. L.; Roberts, L.; Greaney, M. F. Angew. Chem., Int. Ed. 2009, 48, 5199
26. Zhang, F.; Moses, J. E. Org. Lett. 2009, 11, 1587
27. Whilst this manuscript was under review, Shi, Larock and co-workers described the reaction of aldehyde-derived N -tosylhydrazones with arynes to form indazoles: Li, P.; Zhao, J.; Wu, C.; Larock, R. C.; Shi, F. Org. Lett. 2011, ASAP DOI: 10.1021/ol201086g.
28. A conventional Fischer-indole synthesis of N -tosyl indoles would require uncommon N -tosylsulfonyl- N -arylhydrazines as starting materials. Examples of N -benzoyl- N -arylhydrazines undergoing Fischer-indole synthesis to the N -benzoyl indoles are known: Mills, K.; Al Khawaja, I. K.; Al-Saleh, F. S.; Joule, J. A. J. Chem. Soc., Perkin Trans. 1 1981, 2, 636
29. Campos, K. R.; Woo, J. C. S.; Lee, S.; Tillyer, R. D. Org. Lett. 2004, 6, 79
30. Chalmers, J. R.; Openshaw, H. T.; Smith, G. F. J. Chem. Soc. 1957, 1115