A copper-catalyzed C-N bond formation involving sp-hybridized carbons. A direct entry to chiral ynamides via N-alkynylation of amides

Journal of the American Chemical Society

Volumn 125, Issue 9, 2003, Pages 2368-2369

  Frederick, Michael O ^a   Mulder, Jason A ^a   Tracey, Michael R ^a   Hsung, Richard P ^a   Huang, Jian ^a   Kurtz, Kimberly C M ^a   Shen, Lichun ^a   Douglas, Christopher J ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNYL GROUP; AMIDE; CARBON; COPPER; IODINE DERIVATIVE; OXAZOLIDINONE DERIVATIVE; UNCLASSIFIED DRUG; YNAMIDE;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHIRALITY; HYBRIDIZATION; REACTION ANALYSIS; THERMOSTABILITY;

EID: 0037420370     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja021304j     Document Type: Article

References (45)

1. For a review on chemistry of ynamides, see: Zificsak, C. A.; Mulder, J. A.; Hsung, R. P.; Rameshkumar, C.; Wei L.-L. Tetrahedron 2001, 57, 7575.
2. For reviews on ynamines, see: (a) Himbert, G. In Methoden Der Organischen Chemie (Houben-Weyl); Kropf, H., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1993; pp 3267-3443.
3. (b) Collard-Motte, J.; Janousek, Z. Top. Curr. Chem. 1986, 130, 89.
4. (c) Ficini, J. Tetrahedron 1976, 32, 1448.
5. For the first examples of ynamides, see: Janousek, Z.; Collard, J.; Viehe, H. G. Angew. Chem., Int. Ed. Engl. 1972, 11, 917.
6. For other key examples, see: (a) Feldman, K. S.; Bruendl, M. M.; Schildknegt, K.; Bohnstedt, A. C. J. Org. Chem. 1996, 61, 5440.
7. (b) Balsamo, A.; Macchia, B.; Macchia, F.; Rossello, A.; Domiano, P. Tetrahedron Lett. 1985, 26, 4141, and ref 18 therein.
8. (a) Rainier, J. D.; Imbriglio, J. E. J. Org. Chem. 2000, 65, 7272.
9. (b) Rainier, J. D.; Imbriglio, J. E. Org. Lett. 1999, 1, 2037.
10. (a) Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1998, 37, 489.
11. (b) Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1998, 38, 2426.
12. (c) Witulski, B.; Gössmann, M. Chem. Commun. 1999, 1879.
13. (d) Witulski, B.; Gössmann, M. Synlett 2000, 1793.
14. (e) Witulski, B.; Stengel, T.; Fernàndez-Hernàndez, J. M. Chem. Commun. 2000, 1965.
15. (f) Witulski, B.; Buschmann, N.; Bergsträsser, U. Tetrahedron 2000, 56, 8473.
16. Schottelius, M. J.; Chen, P. Helv. Chim. Acta 1998, 81, 2341.
17. Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803.
18. (a) Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; Grebe, T. P. Org. Lett. 2002, 4, 2417.
19. (b) Mulder, J. A.; Hsung, R. P.; Frederick, M. O.; Tracey, M. R.; Zificsak, C. A. Org. Lett. 2002, 4, 1383.
20. (c) Hsung, R. P.; Zificsak, C.; Wei, L.-L.; Douglas, C. J.; Xiong, H.; Mulder, J. Org. Lett. 1999, 1, 1237.
21. For a review, see: Saalfrank, R. W.; Lurz, C. J. In Methoden Der Organischen Chemie (Houben-Weyl); Kropf, H., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1993; p 3093.
22. Wei, L.-L.; Mulder, J. A.; Xiong, H.; Zificsak, C. A.; Douglas, C. J.; Hsung, R. P. Tetrahedron 2001, 57, 459.
23. For reviews on palladium-catalyzed N-arylations of amines and amides, see: (a) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046. (b) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. For an earlier account, see: (c) Kosugi, M.; Kameyama, M.; Migita, T. Chem. Lett. 1983, 927.
24. For reviews on palladium-catalyzed N-arylations of amines and amides, see: (a) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046. (b) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. For an earlier account, see: (c) Kosugi, M.; Kameyama, M.; Migita, T. Chem. Lett. 1983, 927.
25. For reviews on palladium-catalyzed N-arylations of amines and amides, see: (a) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046. (b) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. For an earlier account, see: (c) Kosugi, M.; Kameyama, M.; Migita, T. Chem. Lett. 1983, 927.
26. For recent references from Buchwald's lab, see: (a) Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158 and references therein. (b) Yin, J.; Buchwald, S. L. Org. Lett. 2000, 2, 1101. (c) Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 6043.
27. For recent references from Buchwald's lab, see: (a) Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158 and references therein. (b) Yin, J.; Buchwald, S. L. Org. Lett. 2000, 2, 1101. (c) Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 6043.
28. For recent references from Buchwald's lab, see: (a) Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158 and references therein. (b) Yin, J.; Buchwald, S. L. Org. Lett. 2000, 2, 1101. (c) Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 6043.
29. For selected references from the Hartwig lab, see: (a) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 3694. (b) Mann, G.; Hartwig, J. F.; Driver, M. S.; Fernández-Rivas, C. J. Am. Chem. Soc. 1998, 120, 827. (c) Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575.
30. For selected references from the Hartwig lab, see: (a) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 3694. (b) Mann, G.; Hartwig, J. F.; Driver, M. S.; Fernández-Rivas, C. J. Am. Chem. Soc. 1998, 120, 827. (c) Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575.
31. For selected references from the Hartwig lab, see: (a) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 3694. (b) Mann, G.; Hartwig, J. F.; Driver, M. S.; Fernández-Rivas, C. J. Am. Chem. Soc. 1998, 120, 827. (c) Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575.
32. Recent examples: (a) Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Zappia, G. Org. Lett. 2001, 3, 2539.
33. (b) Artamkina, G. A.; Sergeev, A. G.; Beletskaya, I. P. Tetrahedron Lett. 2001, 42, 4381.
34. (c) Edmondson, S. D.; Mastracchio, A.; Parmee, E. R. Org. Lett. 2000, 2, 1109.
35. (d) Bolm, C.; Hildebrand, J. J. Org. Chem. 2000, 65, 169.
36. Results using palladium were carried out three years ago.
37. For a review on copper mediated C-N and C-O bond formation, see: (a) Lindley, J. Tetrahedron 1984, 40, 1433. Also see: (b) Goldberg, I. Ber. Dtsch. Chem. Ges. 1906, 39, 1691.
38. For a review on copper mediated C-N and C-O bond formation, see: (a) Lindley, J. Tetrahedron 1984, 40, 1433. Also see: (b) Goldberg, I. Ber. Dtsch. Chem. Ges. 1906, 39, 1691.
39. Recent key papers from Buchwald's group, see: (a) Klapper, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421. (b) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727. (c) Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581.
40. Recent key papers from Buchwald's group, see: (a) Klapper, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421. (b) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727. (c) Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581.
41. Recent key papers from Buchwald's group, see: (a) Klapper, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421. (b) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727. (c) Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581.
42. For recent references of copper-catalyzed N-arylations of amides and enamides: (a) Shen, R.; Porco, J. A., Jr. Org. Lett. 2002, 2, 1333. (b) Yamada, K.; Kubo, T.; Tokuyama, H.; Fukuyama, T. Synlett 2002, 231. (c) Lam, P. Y. S.; Deudon, S.; Averill, K. M.; Li, R.; He, M. Y.; DeShong, P.; Clark, C. G. J. Am. Chem. Soc. 2000, 122, 7600.
43. For recent references of copper-catalyzed N-arylations of amides and enamides: (a) Shen, R.; Porco, J. A., Jr. Org. Lett. 2002, 2, 1333. (b) Yamada, K.; Kubo, T.; Tokuyama, H.; Fukuyama, T. Synlett 2002, 231. (c) Lam, P. Y. S.; Deudon, S.; Averill, K. M.; Li, R.; He, M. Y.; DeShong, P.; Clark, C. G. J. Am. Chem. Soc. 2000, 122, 7600.
44. For recent references of copper-catalyzed N-arylations of amides and enamides: (a) Shen, R.; Porco, J. A., Jr. Org. Lett. 2002, 2, 1333. (b) Yamada, K.; Kubo, T.; Tokuyama, H.; Fukuyama, T. Synlett 2002, 231. (c) Lam, P. Y. S.; Deudon, S.; Averill, K. M.; Li, R.; He, M. Y.; DeShong, P.; Clark, C. G. J. Am. Chem. Soc. 2000, 122, 7600.
45. 23D.