Halopalladation/decarboxylation/carbon-carbon forming domino process: synthesis of 5-halo-6-substituted benzo[b]naphtho[2,1-d]furans

Organic Letters

Volumn 11, Issue 5, 2009, Pages 1139-1142

  Huang, Xiao Cheng ^a   Wang, Feng ^a   Liang, Yun ^a   Li, Jin Heng ^a,b  

^a HUNAN NORMAL UNIVERSITY   (China)

^b WENZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; BENZOFURAN DERIVATIVE; BROMINE; CHLORINE; FUSED HETEROCYCLIC RINGS; HALOGENATED HYDROCARBON; NAPHTHALENE DERIVATIVE; PALLADIUM;

ARTICLE; CHEMISTRY; COMBINATORIAL CHEMISTRY; SYNTHESIS;

ALKYNES; BENZOFURANS; BROMINE; CHLORINE; COMBINATORIAL CHEMISTRY TECHNIQUES; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; HYDROCARBONS, HALOGENATED; NAPHTHALENES; PALLADIUM;

EID: 64349096189     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8029752     Document Type: Article

References (40)

1. For reviews, see: (a) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: New York, 1985.
2. (b) Tsuji, J. Palladium Reagents and Catalysts: InnoVations in Organic Synthesis; Wiley and Sons: New York, 1995.
3. (c) Li, J. J.; Gribble, G. W. Palladium in Heterocyclic Chemistry; Pergamon: New York, 2000.
4. (d) Lu, X. Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002; Vol. 2, pp 2267-2288.
5. (e) Han, X. L.; Liu, G. X.; Lu, X. Y. Chin. J. Org. Chem. 2005, 25, 1182.
6. (f) Tang, S.; Wang, N.-X.; Li, J.-H. Chin. J. Org. Chem. 2007, 27, 819.
7. Phillips, F. C. Z. Anorg. Allg. Chem. 1894, 6, 229.
8. (a) Liang, Y.; Tang, S.; Zhang, X.-D.; Mao, L.-Q.; Xie, Y.-X.; Li, J.-H. Org. Lett. 2006, 8, 3017.
9. (b) Tang, S.; Xie, Y.-X.; Li, J.-H.; Wang, N.-X. Synthesis 2007, 1841.
10. (c) Tang, S.; Yu, Q.-F.; Peng, P.; Li, J.-H.; Zhong, P.; Tang, R.-Y. Oeg. Lett. 2007, 9, 3413.
11. 2 as a catalytic system, see:
12. (a) Bäckvall, J. E.; Nordberg, R. E. J. Am. Chem. Soc. 1980, 102, 393.
13. (b) Ji, J.; Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 1160.
14. (c) Ma, S.; Lu, X. J. Org. Chem. 1993, 58, 1245.
15. (d) Li, J.-H; Jiang, H.-F.; Feng, A.-Q.; Jia, L.-Q. J. Org. Chem. 1999, 64, 5984.
16. (e) Li, J.-H.; Jiang, H.-F.; Chen, M.-C. J. Org. Chem. 2001, 66, 3627.
17. (f) Li, J.-H.; Liang, Y.; Xie, Y.-X. J. Org. Chem. 2004, 69, 8125.
18. (g) Li, J.-H.; Tang, S.; Xie, Y.-X. J. Org. Chem. 2005, 70, 477.
19. (h) Ma, S.; Wu, B.; Zhao, S. Org. Lett. 2003, 5, 4429.
20. (i) Ma, S.; Wu, B.; Jiang, X.; Zhao, S. J. Org. Chem. 2005, 70, 2568.
21. (j) Ma, S.; Wu, B.; Jiang, X. J. Org. Chem. 2005, 70, 2588.
22. (k) Huang, J.; Zhou, L.; Jiang, H. Angew. Chem., Int. Ed. 2006, 45, 1945.
23. For selected reviews and papers on Pd-catalyzed decarboxylative coupling reactions, see:
24. (a) Goossen, L. J.; Goossen, K.; Rodríguez, N.; Blanchot, M.; Linder, C.; Zimmermann, B. Pure Appl. Chem. 2008, 80, 1725.
25. (b) Goossen, L. J.; Rodríguez, N.; Goossen, K. Angew. Chem., Int. Ed. 2008, 47, 3100, and references cited therein.
26. (c) Tatamidani, H.; Yokota, K.; Kakiuchi, F.; Chatani, N. J. Org. Chem. 2004, 69, 5615.
27. (d) Goossen, L. J.; Knauber, T. J. Org. Chem. 2008, 73, 8631.
28. (e) Goossen, L. J.; Zimmermann, B.; Knauber, T. Angew. Chem., Int. Ed. 2008, 47, 7103.
29. (f) Goossen, L. J.; Rodríguez, N.; Linder, C. J. Am. Chem. Soc. 2008, 130, 15248.
30. (g) Goossen, L. J.; Rudolphi, F.; Oppel, C.; Rodríguez, N. Angew. Chem., Int. Ed. 2008, 47, 3043.
31. (h) Maehara, A.; Tsurugi, H.; Satoh, T.; Miura, M. Org. Lett. 2008, 10, 1259.
32. (i) Nakano, M.; Tsurugi, H.; Satoh, T.; Mura, M. Org. Lett. 2008, 10, 1851.
33. (j) Forgione, P.; Brochu, M.-C.; St-Onge, M.; Thesen, K. H.; Bailey, M. D.; Bilodeau, F. J. Am. Chem. Soc. 2006, 128, 11350.
34. (a) Harvey, R. G. Polycyclic Aromatic Hydeocarbons; Wiley-VCH: New York, 1996.
35. (b) Harvey, R. G. In Handbook of Environmental Chemistry; Hutzinger, D., Neilson, A., Eds.; Springer: Berlin, Heidelberg, 1997; Vol. 3, part 1, ch. 1.
36. (c) Watson, M. D.; Fechtenkotter, A.; Mullen, K. Chem. Rev. 2001, 101, 1267.
37. (d) Law, K. Y. Chem. Rev. 1993, 93, 449.
38. (e) Jung, M. E. Tetrahedron 1976, 32, 3.
39. (f) Molander, G. A. Acc. Chem Res. 1998, 31, 603.
40. (g) Tiwari, S. S.; Srivastava, S. C. J. Med. Chem. 1967, 10, 983.