Efficient syntheses of heterocycles and carbocycles by electrophilic cyclization of acetylenic aldehydes and ketones

Organic Letters

Volumn 6, Issue 10, 2004, Pages 1581-1584

  Yue, Dawei ^a   Della Cà, Nicola ^a   Larock, Richard C ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; ALDEHYDE DERIVATIVE; ALKYNE DERIVATIVE; BROMINE DERIVATIVE; CARBON; CARBONYL DERIVATIVE; CHLORINE DERIVATIVE; HETEROCYCLIC COMPOUND; IODINE; KETONE DERIVATIVE; NAPHTHYL GROUP; SELENIUM DERIVATIVE;

ARTICLE; CYCLIZATION; ROOM TEMPERATURE; SUBSTITUTION REACTION; SYNTHESIS;

EID: 2542606253     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049690s     Document Type: Article

References (43)

1. (a) Lotagawa, O.; Inoue, T.; Taguchi, T. Rev. Heteroatom Chem. 1996, 15, 243.
2. (b) Frederickson, M.; Grigg, R. Org. Prep. Proc. Int. 1997, 29, 33.
3. (c) Cardillo, G.; Orena, M. Tetrahedron 1990, 46, 3321.
4. (a) Drenth, W. In Chemistry of Triple-Bonded Functional Groups; Patai, S., Ed.; J. Wiley: Chichester, UK, 1994; Vol. 2, pp 873-915.
5. (b) Schmid, G. H. In The Chemistry of the Carbon-Carbon Triple Bond; Patai, S., Ed.; J. Wiley: Chichester, UK, 1978; Vol. 1, pp 275-341.
6. Yue, D.; Larock, R. C. J. Org. Chem. 2002, 67, 1905.
7. Huang, Q.; Hunter, J. A.; Larock, R. C. J. Org. Chem. 2002, 67, 3437.
8. Yao, T.; Larock, R. C. Tetrahedron Lett. 2002, 43, 7401.
9. (a) Barluenga, J.; Trincado, M.; Rubio, E.; Gonza'lez, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406.
10. (b) Knight, D. W.; Redfern, A. L.; Gilmore, J. J. Chem. Soc., Perkin Trans. 1 2002, 622.
11. (c) Arcadi, A.; Cacchi, S.; Giuseppe, S. D.; Fabrizi, G.; Marinelli, F. Org. Lett. 2002, 4, 2409.
12. (d) Bellina, F.; Biagetti, M.; Carpita, A.; Rossi, R. Tetrahedron Lett. 2001, 42, 2859.
13. (e) Bellina, F.; Biagetti, M.; Carpita, A.; Rossi, R. Tetrahedron 2001, 57, 2857.
14. (f) Flynn, B. L.; Verdier-Pinard, P.; Hamel, E. Org. Lett. 2001, 5, 651.
15. (g) Djuardi, E.; McNelis, E. Tetrahedron Lett. 1999, 40, 7193.
16. (h) Marshall, J. A.; Yanik, M. M. J. Org. Chem. 1999, 64, 3798.
17. (i) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L. Synlett 1999, 1432.
18. (j) Knight, D. W.; Redfern, A. L.; Gilmore, J. J. Chem. Soc., Chem. Commun. 1998, 2207.
19. (k) Redfern, A. L.; Gilmore, J. Synlett 1998, 731.
20. (l) Ren, X.-F.; Konaklieva, M. I.; Shi, H.; Dicy, H.; Lim, D. V.; Gonzales, J.; Turos, E. J. Org. Chem. 1998, 63, 8898.
21. (m) Bew, S. P.; Knight, D. W. J. Chem. Soc., Chem. Commun. 1996, 1007.
22. (n) El-Taeb, G. M. M.; Evans, A. B.; Jones, S.; Knight, D. W. Tetrahedron Lett. 2001, 42, 5945.
23. (a) Asao, N.; Nogami, T.; Takahashi, K.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 764.
24. (b) Nakamura, H.; Ohtaka, M.; Yamamoto, Y. Tetrahedron Lett. 2002, 43, 7631.
25. Barluenga, J.; Vazquez-Villa, H.; Ballesteros, A.; Gonzalez, J. M. J. Am. Chem. Soc. 2003, 125, 9028.
26. For a recent review on multicomponent reactions, see, for instance: Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168.
27. Tovar, J. D.; Swager, T. M. J. Org. Chem. 1999, 64, 6499.
28. (a) Sonogashira, K. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; Chapter 5, pp 203-229.
29. (b) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467.
30. (a) Asao, N.; Takahashi, K.; Lee, S.; Kasahara, T.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 12650.
31. (b) Asao, N.; Nogami, T.; Lee, S.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 10921.
32. (c) Asao, N.; Kasahara, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2003, 42, 3504.
33. (d) Barluenga, J.; Vazquez-Villa, H.; Ballesteros, A.; Gonzalez, J. M. Org. Lett. 2003, 5, 4121.
34. (a) Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
35. (b) Lloyd-Williams, P.; Giralt, E. Chem. Soc. Rev. 2001, 30, 145.
36. (c) Suzuki, A. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; pp 49-97.
37. (d) Miyaura, N. Chem. Rev. 1995, 95, 2457.
38. (a) Negishi, E.; Dumond, Y. Handbook of Organopalladium Chemistry for Organic Synthesis; 2002; Vol. 1, p 767.
39. (b) Kosugi, M.; Fugami, K. Handbook of Organopalladium Chemistry for Organic Synthesis; 2002; Vol. 1, p 263.
40. (c) Kosugi, M.; Fugami, K. J. Organomet. Chem. 2002, 653, 50.
41. (a) Crisp, G. T. Chem. Soc. Rev. 1998, 27, 427.
42. (b) Brase, S.; De Meijere, A. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; pp 99-166.
43. (c) Palladium Reagents in Organic Synthesis; Heck, R. F., Ed.; Academic Press: San Diego, 1985; pp 276-287.