Direct transition-metal-free intramolecular arylation of phenols

Organic Letters

Volumn 10, Issue 20, 2008, Pages 4625-4628

  Bajracharya, Gan B ^a   Daugulis, Olafs ^a  

^a University of Houston   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

METAL; PHENOL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY;

METALS; MOLECULAR STRUCTURE; PHENOLS;

EID: 58149166500     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801897m     Document Type: Article

References (43)

1. (a) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.
2. (b) Kakiuchi, F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077.
3. (c) Dick, A. R.; Sanford, M. S. Tetrahedron 2006, 62, 2439.
4. (d) Yu, J.-Q.; Giri, R.; Chen, X. Org. Biomol. Chem. 2006, 4, 4041.
5. (e) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174.
6. (f) Ackermann, L. Synlett 2007, 507.
7. (a) Metal-catalyzed cross-coupling reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: New York, 1998.
8. (b) Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
9. (a) Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1698.
10. (b) Campeau, L.-C; Fagnou, K. Chem. Commun. 2006, 1253.
11. (c) Daugulis, O.; Zaitsev, V. G.; Shabashov, D.; Pham, Q.-N.; Lazareva, A. Synlett 2006, 3382.
12. (d) Seregin, I. V.; Gevorgyan, V. Chem. Soc. Rev. 2007, 36, 1173.
13. (a) Lazareva, A.; Daugulis, O. Org. Lett. 2006, 8, 5211.
14. (b) Chiong, H. A.; Daugulis, O. Org. Lett. 2007, 9, 1449.
15. (c) Chiong, H. A.; Pham, Q.-N.; Daugulis, O. J. Am. Chem. Soc. 2007, 129, 9879.
16. (d) Shabashov, D.; Daugulis, O. J. Org. Chem. 2007, 72, 7720.
17. (a) Do, H.-Q.; Daugulis, O. J. Am. Chem. Soc. 2007, 129, 12404.
18. (b) Do, H.-Q.; Daugulis, O. J. Am. Chem. Soc. 2008, 130, 1128.
19. Hennings, D. D.; Iwasa, S.; Rawal, V. H. J. Org. Chem. 1997, 62, 2.
20. Campeau, L.-C.; Parisien, M.; Jean, A.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 581.
21. (a) Rosa, A. M.; Lobo, A. M.; Branco, P. S.; Prabhakar, S. Tetrahedron 1997, 53, 285.
22. (b) Bowman, W. R.; Mann, E.; Parr, J. J. Chem. Soc., Perkin Trans, 1 2000, 2991.
23. (a) Hrutford, B. F.; Bunnett, J. F. J. Am. Chem. Soc. 1958, 80, 2021.
24. (b) Bunnett, J. F.; Skorcz, J. A. J. Org. Chem. 1962, 27, 3836.
25. (a) Huisgen, R.; König, H. Angew. Chem. 1957, 69, 268.
26. (b) Huisgen, R.: Sauer, J. Angew. Chem. 1960, 72, 91.
27. (c) Huisgen, R.; König. H.; Lepley, A. R. Chem. Ber. 1960, 93, 1496.
28. For general reviews: (a) Kessar, S. V. Acc. Chem. Res. 1978, 11, 283.
29. (b) Biehl, E. R.; Khanapure, S. P. Acc. Chem. Res. 1989, 22, 275.
30. (c) Pellissier, H.; Santelli, M. Tetrahedron, 2003, 59, 701.
31. Benzyne reactions with Pd species: (d) Liu, Z.; Larock, R. C. J. Org. Chem. 2007, 72, 223.
32. Sielecki, T. M.; Meyers, A. I. J. Org. Chem. 1992, 57, 3673.
33. Bunnett, J. F.; Hrutfiord, B. F. J. Am. Chem. Soc. 1961, 83, 1691.
34. Clark, R. D.; Caroon, J. M. J. Org. Chem. 1982, 47, 2804.
35. Knight, D. W.; Little, P. B. Synlett 1998, 1141.
36. (a) Stanetty, P.; Krumpak, B. J. Org. Chem. 1996, 61, 5130.
37. (b) Fairhurst, R. A.; Janus, D.; Lawrence, A. Org. Lett. 2005, 7, 4697.
38. Iwao, M. J. Org. Chem. 1990, 55, 3622.
39. (a) Kessar, S. V.; Gupta, Y. P.; Balakrishnan, P.; Sawal, K. K.; Mohammad, T.; Dutt, M. J. Org. Chem. 1988, 53, 1708.
40. (b) Kametani, T.; Shibuya, S.; Kigasawa, K.; Hiiragi, M.; Kusama, O. J. Chem. Soc. C 1971, 2712.
41. (c) Kessar, S. V.; Randhawa, R.; Gandhi, S. S. Tetrahedron Lett. 1973, 14, 2923.
42. Sanz, R.; Fernández, Y.; Castroviejo, M. P.; Pérez, A.; Fanǎnás, F. J. Eur. J. Org. Chem. 2007, 62.
43. It has been shown that ppb to ppm level palladium contaminants in commercial bases allows cross-coupling reactions to proceed without adding transition-metal catalysts. However, (1) aryl chlorides should not be reactive under such conditions (Table 2, entry 3), (2) deuterium incorporation in 10-position of the product would not be observed if the reactions proceed by conventional cross-coupling pathways (Scheme 2), and (3) the cyclization is less regioselective compared with Rawal's Pd-catalyzed method (ref 6). Arvela, R. K.; Leadbeater, N. E.; Sangi, M. S.; Williams, V. A.; Granados, P.; Singer, R. D. J. Org. Chem. 2005, 70, 161.