Water-triggered, counter-anion-controlled, and silver-phosphines complex-catalyzed stereoselective cascade alkynylation/cyclization of terminal alkynes with salicylaldehydes

Journal of Organic Chemistry

Volumn 74, Issue 9, 2009, Pages 3378-3383

  Yu, Min ^a   Skouta, Rachid ^b   Zhou, Lei ^b,c   Jiang, Huan Feng ^c   Yao, Xiaoquan ^a   Li, Chao Jun ^b  

^a NANJING UNIVERSITY OF AERONAUTICS AND ASTRONAUTICS   (China)

^b MCGILL UNIVERSITY   (Canada)

^c SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNYLATION; CASCADE REACTIONS; COUNTER ANIONS; KEY FACTORS; SALICYL ALDEHYDE; SILVER COMPLEXES; STEREO-SELECTIVE; TERMINAL ALKYNE;

ACETYLENE; NEGATIVE IONS; PHOSPHORUS COMPOUNDS; SILVER; SILVER COMPOUNDS; STEREOSELECTIVITY;

ORGANIC POLYMERS;

ALKYNE; ANION; DIHYDROBENZOFURAN DERIVATIVE; PHOSPHINE DERIVATIVE; SALICYLALDEHYDE; SILVER; WATER;

ALKYNYLATION; ARTICLE; CATALYST; CHEMICAL PARAMETERS; CHEMICAL STRUCTURE; CYCLIZATION; OXIDATION; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 66449090967     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900079u     Document Type: Article

References (47)

1. (a) For recent reviews on C-H activations, see: Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1698.
2. Chatani, N.; Asaumi, T.; Yorimitsu, S.; Ikeda, T.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 2001, 123, 10935.
3. Chen, H.; Schlecht, S.; Semple, T. C.; Hartwig, J. F. Science 2000, 287, 1995.
4. Goldman, A. S. Nature (London) 1993, 366, 514.
5. Crabtree, R. H. J. Organomet. Chem. 2004, 689, 4083.
6. (f) Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633.
7. (b) For atom-economy, see: Trost, B. M. Science 1991, 254, 1471.
8. Trost, B. M. Angew. Chem., Int. Ed. 1995, 34, 259.
9. Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and Practice; Oxford University Press, New York, 2000.
10. For Grignard-type reactions utilizing C-H bonds directly in water, see: Herrerías, C. I.; Yao, X.; Li, Z.; Li, C.-J. Chem. Rev. 2007, 107, 2546.
11. For a review, see: Cozzi, P. G.; Hilgraf, R.; Zimmermann, N. Eur. J. Org. Chem. 2004, 4095.
12. For a recent example, see: (a) Kang, Y.-F.; Wang, R.; Liu, L.; Da, C.-S.; Yan, W.-J.; Xu, Z.-Q. Tetrahedron Lett. 2005, 46, 863.
13. (b) Fang, T.; Du, D.-M.; Lu, S.-F.; Xu, J.-X. Org. Lett. 2005, 7, 2081.
14. For a review on the zinc acetylide system, see: (a) Frantz, D. E.; Fässler, R.; Tomooka, C. S.; Carreira, E. M. Acc. Chem. Res. 2000, 33, 373.
15. For a catalytic system, see: (b) Anand, N. K.; Carreira, E. M. J. Am. Chem. Soc. 2001, 123, 9687.
16. (c) Fässler, R.; Tomooka, C. S.; Frantz, D. E.; Carreira, E. M. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5843.
17. See also: (d) Jiang, B.; Chen, Z.; Tang, X. Org. Lett. 2002, 4, 3451.
18. For stoichiometric additions to aldehyde, see: (f) Frantz, D. E.; Fässler, R.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 1806.
19. (g) Boyall, D.; Frantz, D. Z.; Carreira, E. M. Org. Lett. 2002, 4, 2605.
20. Takita, R.; Fukuta, Y.; Tsuji, R.; Ohshima, T.; Shibasaki, M. Org. Lett. 2005, 7, 1363.
21. Yao, X.; Li, C.-J. Org. Lett. 2005, 7, 4395.
22. For an account on the addition of terminal alkynes to imines, see: (a) Wei, C.; Li, Z.; Li, C.-J. Synlett 2004, 1472.
23. See also: (b) Wei, C.; Mague, J. T.; Li, C.-J. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5749.
24. (c) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2002, 124, 5683.
25. (d) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2003, 125, 9584.
26. (e) Wei, C.; Li, Z.; Li, C.-J. Org. Lett. 2003, 5, 4473.
27. (f) Li, Z.; Wei, C.; Chen, L.; Varma, R. S.; Li, C.-J. Tetrahedron Lett. 2004, 45, 2443.
28. (g) Li, C.-J.; Wei, C. Chem. Commun 2002, 268.
29. (h) Li, C.-J. Acc. Chem. Res. 2002, 35, 533.
30. (i) Li, C.-J.; Wei, C. Green Chem. 2002, 4, 39.
31. (j) Zani, L.; Bolm, C. Chem. Commun. 2006, 4263.
32. It was widely accepted that metal acetylides generated from Group IB metals could not participate in the nucleophilic CdO addition; see refs 5c and 6.
33. Yao, X.; Li, C.-J. Org. Lett. 2006, 8, 1953.
34. For a review, see: Boumendjel, A. Curr. Med. Chem. 2003, 10, 2621.
35. For selected examples, see: (a) Imafuku, K.; Honda, M.; McOmie, J. F. W. Synthesis 1987, 199.
36. (b) Thakkar, K.; Cushman, M. J. Org. Chem. 1995, 60, 6499.
37. (c) Garcia, H.; Iborra, S.; Primo, J.; Miranda, M. A. J. Org. Chem. 1986, 51, 4432.
38. (d) An, Z.-W.; Catellani, M.; Chiusoli, G. P. J. Organomet. Chem. 1990, 397, 371.
39. (e) Jong, T.-T.; Leu, S.-J. J. Chem. Soc., Perkin Trans. 1 1990, 423.
40. Harkat, H.; Blanc, A.; Weibel, J.-M.; Pale, P. J. Org. Chem. 2008, 73, 1620.
41. For recent reviews on silver-catalyzed reactions, see: (a) Yamamoto, Y. Chem. Rev. 2008, 108, 3199.
42. (b) Weibel, J.-M.; Blanc, A.; Pale, P. Chem. Rev. 2008, 108, 3149.
43. (c) Halbes-Letinois, U.; Weibel, J.-M.; Pale, P. Chem. Soc. Rev. 2007, 36, 759.
44. (d) Li, Z.; He, C. Eur. J. Org. Chem. 2006, 4313-4322.
45. For the heterogeneous reaction on small scales, the substrates tend to stick on the surface of the stirring bar or the side of the tube, which results in lower conversions. The introduction of a lower-boiling solvent such as DCE and methylene chloride together with a higher reaction temperature may be helpful to keep the substrates in the reaction mixture and increase the yield.
46. The E-4a stereochemistry was defined by 1D NOE, irradiating the peaks at 6.53 and 5.94 ppm. For the E-isomer, no NOE effect with each other was observed. Please see the spectra for Z-3a and E-4a in Supporting Information.
47. Fresh MnO2 was prepared from MnSO4 and KMnO4.