Synthesis of Conformationally Restricted 2,3-Diarylbenzo[b]furan by the Pd-Catalyzed Annulation of o-Alkynylphenols: Exploring a Combinatorial Approach

Journal of Organic Chemistry

Volumn 69, Issue 7, 2004, Pages 2235-2239

  Hu, Youhong ^a   Nawoschik, Kenneth J ^a   Liao, Yun ^a   Ma, Jian ^a   Fathi, Reza ^a   Yang, Zhen ^a,b  

^a VivoQuest Inc   (United States)

^b PEKING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CONFORMATIONS; NITROGEN COMPOUNDS; PALLADIUM;

DRUG DISCOVERY; SYNTHETIC PATHWAYS;

SYNTHESIS (CHEMICAL);

ALKYNYL GROUP; AROMATIC HYDROCARBON; BENZOFURAN DERIVATIVE; HALIDE; PALLADIUM; PHENOL DERIVATIVE;

ANNULATION REACTION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; COMBINATORIAL CHEMISTRY; CONFORMATION; DRUG DEVELOPMENT; REACTION ANALYSIS; SYNTHESIS;

BENZOFURANS; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; DRUG DESIGN; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; PALLADIUM; PHENOLS; STEREOISOMERISM;

EID: 1842452756     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0303160     Document Type: Article

References (47)

1. (a) Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H. Comprehensive Asymmetric Catalysis; Springer: Berlin, 1999; Vols. 1-3.
2. (b) Ojima, I., Ed. Catalytic Asymmetric Synthesis, 2nd ed.; Wiley-VCH: New York, 2000.
3. (c) Pu, L. Chem. Rev. 1998, 98, 2405.
4. (d) Noyori, R.; Ohkuma, T. Angew. Chem., Int. Ed. 2001, 40, 40.
5. (a) Williams, D. H.; Bardsley, B. Angew. Chem., Int. Ed. 1999, 38, 1172.
6. (b) Nicolaou, K. C.; Boddy, C. N. C.; Brase, S.; Winssinger, N. Angew. Chem., Int. Ed. 1999, 38, 2096.
7. (a) Larock, R. C.; Yum, E. K.; Doty, M. J.; Sham, K. K. C. J. Org. Chem. 1995, 60, 3270.
8. (b) Hellwinkel, D.; Göke, K. Synthesis 1995, 1135.
9. (c) Katritzky, A. R.; Fali, C. N.; Li, J.-Q. J. Org. Chem. 1997, 62, 8205. Schmittel, M.; Langels, A. J. Org. Chem. 1998, 63, 7328.
10. (c) Katritzky, A. R.; Fali, C. N.; Li, J.-Q. J. Org. Chem. 1997, 62, 8205. Schmittel, M.; Langels, A. J. Org. Chem. 1998, 63, 7328.
11. (d) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L. Synlett 2000, 1432.
12. (e) Dai, W.-M.; Lai, K. W. Tetrahedron Lett. 2002, 43, 9377.
13. (f) Morrison, B. J.; Musgrave, O. C. Tetrahedron 2002, 58, 4255.
14. (g) Arcadi, A.; Cacchi, S.; Gluseppe, S. D.; Fabrizi, G.; Marinelli, F. Org. Lett. 2002, 4, 2409.
15. (a) Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1992, 333, 3915.
16. (b) Cacchi, S.; Carnicelli, V.; Marinelli, F. J. Orgnomet. Chem. 1994, 475, 289.
17. (c) Cacchi, S.; Fabrizi, G.; Moro, L. Tetrahedron Lett. 1998, 63, 5306.
18. (d) Larock, R. C.; Yum, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652.
19. (e) Cacchi, S. J. Organomet. Chem. 1999, 576, 42.
20. (f) Nan, Y.; Miao, H.; Yang, Z. Org. Lett. 2000, 2, 297.
21. (g) Bellina, F.; Biagetti, M.; Carpita, A.; Rossi, R. Tetrahedron 2001, 57, 2857.
22. (h) Flynn, B. L.; Verdier-Pinard, P.; Hamel, E. Org. Lett. 2001, 3, 2973.
23. (i) Roesch, K. R.; Larock, R. C. J. Org. Chem. 2001, 66, 412.
24. (j) Arcadi, A.; Cacchi, S.; Giuseppe, S. D.; Fabrizi, G. Marinelli, F. Synlett 2002, 453.
25. (k) Yue, D.; Larock, R. C. J. Org. Chem. 2002, 67, 1905.
26. (l) Hu, Y.-H.; Zhang, Y.; Yang, Z.; Fathi, R. J. Org. Chem. 2002, 67, 2365.
27. Arcadi, A.; Cacchi, S.; Rosario, M. D.; Fabrizi, G.; Marinelli, F. J. Org. Chem. 1996, 61, 9280.
28. (a) Chaplin, J. H.; Flynn, B. L. Chem. Commun. 2001, 1594.
29. (b) Flynn, B. L.; Hamel, E.; Jung, M. K. J. Med. Chem. 2002, 45, 2670.
30. (a) Nan, Y.; Miao, H.; Yang, Z. Org. Lett. 2000, 2, 297.
31. (b) Hu, Y.-H.; Yang, Z. Org. Lett. 2001, 3, 1387.
32. (c) Liao, Y.; Fathi, R.; Reitman, M.; Zhang, Y.; Yang, Z. Tetrahedron Lett. 2001, 42, 1815.
33. (d) Hu, Y.-H.; Zhang, Y.; Yang, Z.; Fathi, R. J. Org. Chem. 2002, 67, 2365.
34. (e) Liao, Y.; Reitman, M.; Zhang, Y.; Fathi, R.; Yang, Z. Org. Lett. 2002, 4, 2607.
35. (e) Liao, Y.; Fathi, R.; Yang, Z. Org. Lett. 2003, 5, 909.
36. (f) Liao, Y.; Fathi, R.; Yang, Z. J. Comb. Chem. 2003, 5, 79.
37. Liao, Y.; Hu, Y.-H.; Wu, J.; Zhu, Q.; Donovan, M.; Fathi, R.; Yang, Z. Curr. Med. Chem. 2003, 10, 2285.
38. (a) Sinner, F.; Buchmeiser, M. R.; Tessadri, R.; Mupa, M.; Wurst, K.; Bonn, G. K. J. Am. Chem. Soc. 1998, 120, 2790.
39. (b) Wu, G. G.; Wong, Y.-S.; Poirier, M. Org. Lett. 1999, 1, 745.
40. (c) Buchmeiser, M. R.; Wurst, K. J. Am. Chem. Soc. 1999, 121, 11101.
41. (d) Yagyu, T.; Osakada, K. Organometallics 2000, 19, 2125.
42. (e) Silberg, J.; Schareina, T.; Kempe, R.; Wurst, K.; Buchmeiser, M. R. J. Organomet. Chem. 2001, 622, 6.
43. (f) Buchmeiser, M. R.; Schareina, T.; Kempe, R.; Wurst, K. J. Organomet. Chem. 2001, 634, 39.
44. (g) Mubofu, E. B.; Clark, J. H.; Macquarrie, D. J. Green Chem. 2001, 3, 1077.
45. Tallarico, J. A.; Depew, K. M.; Pelish, H. E.; Westwood, N. J.; Lindsley, C. W.; Shair, M. D.; Schreiber, S. L.; Foley, M. A. J. Chem. Chem. 2001, 3, 312.
46. Nicolaou, K. C.; Xiao, X.-Y.; Parandoosh, Z.; Senyei, A.; Nova, M. P. Angew. Chem., Int. Ed. 1995, 34, 2289-2291.
47. During preparation of our manuscript, a related paper was published: Bossharth, E.; Desbordes, P.; Monteiro, N.; Balme, G. Org. Lett. 2003, 5, 2441. The paper reported a similar approach to synthesize furo[2,3-b]pyridones by one-pot coupling of 3-iodopyridones, alkynes, and organic halides. The authors proposed that the complexation of palladium catalyst to the o-alkoxy group on the phenyl ring might contribute to generation of the desired compounds, which might limit the scope of substrate for the reaction.