Water-triggered and gold(I)-catalyzed cascade addition/cyclization of terminal alkynes with ortho-alkynylaryl aldehyde

Organic Letters

Volumn 8, Issue 9, 2006, Pages 1953-1955

  Yao, Xiaoquan ^a   Li, Chao Jun ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33646447353     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060645p     Document Type: Article

References (50)

1. (a) For a recent review, see: Dyker, G. Angew. Chem. Int. Ed. 1999, 38, 1698.
2. (b) Trost, B. M. Acc. Chem. Res. 2002, 35, 695.
3. For representative reviews, see: (a) Li, C.-J. Chem. Rev. 1993, 93, 2023.
4. (b) Lindstrom, U. M. Chem. Rev. 2002, 102, 2751.
5. (c) Li, C.-J. Chem. Rev. 2005, 105, 3095.
6. For the Grignard-type reaction in water, see: (d) Li, C.-J. Green Chem. 2002, 4, 1.
7. (e) Li, C.-J. Tetrahedron 1996, 52, 5643.
8. (a) Biber, B.; Muske, J.; Ritzan, M.; Graft, U. J. Antibiot. 1998, 51, 381.
9. (b) Maruse, N.; Goto, M. J. Antibiot. 1998, 51, 545.
10. (c) Wang, W.; Breining, T.; Li, T.; Milbum, R.; Attardo, G. Tetrahedron Lett. 1998, 39, 2459 and the references therein.
11. For representative examples, see: (a) Asao, N.; Nogami, T.; Takahashi, K.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 764.
12. (b) Patil, N. T.; Yamamoto, Y. J. Org. Chem. 2004, 69, 5139.
13. (c) Nakamura, H.; Ohtaka, M.; Yamamoto, Y. Tetrahedron Lett. 2002, 43, 7631.
14. (d) Asao, N.; Chan, C. S.; Takahashi, K.; Yamamoto, Y. Tetrahedron 2005, 61, 11322.
15. (e) Patil, N. T.; Pahadi, N. K.; Yamamoto, Y. J. Org. Chem. 2005, 70, 10096.
16. (f) Wei, L.-L.; Wei, L.-M.; Pan, W.-B.; Wu, M.-J. Synlett 2004, 1497.
17. Some examples for the electrophilic cyclization: (g) Barluenga, J.; Vazquez-Villa, H.; Ballesteros, A.; Gonzalez, J. M. J. Am. Chem. Soc. 2003, 125, 9028.
18. (h) Yue, D.; Ca, N. D.; Larock, R. C. Org. Lett. 2004, 6, 1581.
19. In the reaction using acetylenic imines as substrates to prepare dihydroisoquinolines, one example with terminal alkynes was reported. Asao, N.; Yudha S. S.; Nogami, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2005, 44, 5526.
20. Yao, X.; Li, C.-J. Org. Lett. 2005, 7, 4395.
21. For an account of the reaction, see: (a) Wei, C.; Li, Z.; Li, C.-J. Synlett 2004, 1472.
22. See also: (b) Wei, C.; Mague, J. T.; Li, C.-J. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5749.
23. (c) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2002, 124, 5683.
24. (d) Wei, C. M.; Li, C.-J. J. Am. Chem. Soc. 2003, 125, 9584.
25. (e) Wei, C.; Li, Z.; Li, C.-J. Org. Lett. 2003, 5, 4473.
26. (f) Li, Z.; Wei, C.; Chen, L.; Varma, R. S.; Li, C.-J. Tetrahedron Lett. 2004, 45, 2443.
27. (g) Li, C.-J.; Wei, C. Chem. Commun. 2002, 268.
28. (h) Li, C.-J. Acc. Chem. Res. 2002, 35, 533.
29. (i) Li, C.-J.; Wei, C. Green Chem. 2002, 39.
30. It was widely accepted that metal acetylides generated from Group IB metals could not participate in the nucleophilic C=O addition. See: (a) Fässler, R.; Tomooka, C. S.; Frantz, D. E.; Carreira, E. M. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5843.
31. (b) Takita, R.; Fukuta, Y.; Tsuji, R.; Ohshima, T.; Shibasaki, M. Org. Lett. 2005, 7, 1363.
32. 3PAuCl-catalyzed reactions, see: (a) Johansson, M. J.; Gorin, D. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 18002.
33. (b) Gorin, D. J.; Davis, N. R.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 11260.
34. (c) Markham, J. P.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 9708.
35. (d) Shi, X.; Gorin, D. J.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 5802.
36. (e) Yang, C.-G.; He, C. J. Am. Chem. Soc. 2005, 127, 6966.
37. (f) Zhang, J.; Yang, C.-G.; He, C. J. Am. Chem. Soc. 2006, 128, 1798.
38. (g) Brouwer, C.; He, C. Angew. Chem., Int. Ed. 2006, 45, early view.
39. (h) Han, X.; Widenhoefer, R. A. Angew. Chem., Int. Ed. 2006, 45, early view.
40. For representative reviews on gold-catalyzed reactions, see: (i) Hashmi, A. S. K. Gold Bull. 2003, 36, 3.
41. (j) Hashmi, A. S. K. Gold Bull. 2004, 37, 51.
42. (k) Hashmi, A. S. K. Angew. Chem., Int. Ed. 2005, 44, 6990.
43. (l) Ma, S.; Gu, Z. Angew. Chem., Int. Ed. 2006, 45, 200.
44. (a) Asao, N.; Nogami, T.; Lee, S.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 10921.
45. (b) Asao, N.; Sato, K.; Menggenbateer; Yamamoto, Y. J. Org. Chem. 2005, 70, 3682.
46. For reactions at small scales, the substrates tend to stick on the surface of the stir bar or on the side of the tube, which results in lower conversions. Adding toluene as a cosolvent avoids such a problem.
47. Asao, N.; Asano, T.; Ohishi, T.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 4817.
48. Another possible mechanism might involve the formation of a benzopyrylium cation (especially in the benzannulation of o-alkynyl(oxo)benzenes with alkynes). See refs 4e and 10; for other recent related examples, see: (a) Buzas, A.; Gagosz, F. Org. Lett. 2006, 8, 515.
49. (b) Kusama, H.; Miyashita, Y.; Takaya, J.; Iwasawa, N. Org. Lett. 2006, 8, 289. However, in all these cases, high-valent metals and/or noncoordinating anions are required.
50. 3P gives the best results.