Palladium(II)-Catalyzed Three-Component Coupling Reaction Initiated by Acetoxypalladation of Alkynes: An Efficient Route to γ,δ-Unsaturated Carbonyls

Organic Letters

Volumn 4, Issue 22, 2002, Pages 3903-3906

  Zhao, Ligang ^a   Lu, Xiyan ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0345966680     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026741h     Document Type: Article

References (47)

1. (a) Ho, T.-L. Tandem Organic Reactions; Wiley-Interscience: New York, 1992.
2. (b) Bunce, R. A. Tetrahedron 1995, 51, 13103.
3. (a) Trost, B. M.; Fleming, I. Comprehensive Organic Synthesis: Selectivity, Strategy and Efficiency in Modern Organic Chemistry; Pergamon: Oxford, UK, 1991; Vol. 3, p 413.
4. (b) Trost B. M.; Pinkerton, A. B. J. Am. Chem. Soc. 2000, 122, 8081 and references therein.
5. (a) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987.
6. (b) Tsuji, J. Palladium Reagents and Catalysts, Innovations in Organic Synthesis; John Wiley: Chichester, UK, 1995.
7. (c) Negishi, E.-I.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365.
8. (d) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
9. (a) Maitlis, P. M. The Organic Chemistry of Palladium; Academic Press: New York, 1971; Vol. 1, p 79.
10. (b) Maitlis, P. M. Acc. Chem. Res. 1976, 9, 93-99.
11. (c) Kaneda, K.; Uchiyama, T.; Fujiwara, Y.; Imanaka, T.; Teranishi, S. J. Org. Chem. 1979, 44, 55.
12. (d) Lambert, C.; Utimoto K.; Nozaki, H. Tetrahedron Lett. 1984, 25, 5323.
13. (e) Yanagihara, N.; Lambert, C.; Iritani, K.; Utimoto, K.; Nozaki, H. J. Am. Chem. Soc. 1986, 108, 2753.
14. (f) Bäckvall, J.-E.; Nilsson, Y. I. M.; Andersson, P. G.; Gatti, R. G. P.; Wu, J. Tetrahedron Lett. 1994, 35, 5713.
15. (g) Bäckvall, J.-E.; Nilsson, Y. I. M.; Gatti, R. G. P. Organometallics 1995, 14, 4242.
16. (h) Lu, X.; Ma, S. New Age of Divalent Palladium Catalysis. In Transition Metal Catalyzed Reaction; Murahashi, S.-I., Davies, S. G., Eds.; Blackwell Science: Oxford, UK, 1999; Chapter 6, p 133.
17. (i) Lu, X.; Zhu, G.; Wang, Z. Synlett 1998, 115.
18. (a) Jonasson, C.; Howath, A.; Bäckvall, J.-E. J. Am. Chem. Soc. 2000, 122, 9600.
19. (b) Bäckvall, J.-E.; Jonasson, C. Tetrahedron Lett. 1997, 38, 291.
20. (c) Kimura, M.; Saeki, N.; Uchida, S.; Harayama, H.; Tanaka, S.; Fugami, K.; Tamaru, Y. Tetrahedron Lett. 1993, 34, 7611.
21. (d) Walkup, R. D.; Mosher, M. D. Tetrahedron 1993, 49, 9285.
22. (e) Gallagher, T.; Davies, I. W.; Jones, S. W.; Lathbury, D.; Mahon, M. F.; Molloy, K. C.; Shaw, R. W.; Vernon, P. J. Chem. Soc., Perkin, Trans. 1 1992, 433.
23. (f) Andersson, P. G.; Bäckvall, J.-E. J. Am. Chem. Soc. 1992, 114, 8696.
24. (g) Walkup, R. D.; Park, G. Tetrahedron Lett. 1987, 28, 1023.
25. (h) Hegedus, L. S.; Kambe, N.; Ishii, Y.; Mori, A. J. Org. Chem. 1985, 50, 2240.
26. (i) Alper, H.; Hartstock, F. W.; Despeyroux, B. J. Chem. Soc., Chem. Commun. 1984, 905.
27. (a) Wang, Z.; Lu, X. J. Chem. Soc., Chem. Commun. 1996, 535.
28. (b) Wang, Z.; Lu, X. J. Org. Chem. 1996, 61, 2254.
29. (c) Wang, Z.; Lu, X.; Lei, A.; Zhang, Z. J. Org. Chem. 1998, 63, 3806.
30. (d) Xie, X.; Lu, X. Synlett 2000, 707.
31. (e) Lei, A.; Lu, X. Org. Lett. 2000, 2, 2699.
32. (f) Liu, G.; Lu, X. Org. Lett. 2001, 3, 3879.
33. (g) Lei, A.; Liu, G.; Lu, X. J. Org. Chem. 2002, 67, 974.
34. In the Pd(II)-catalyzed coupling reactions, the halide ion can block the β-H elimination of a carbon-palladium bond, giving preferentially the protonolysis or β-heteroatom elimination product, see: (a) Wang, Z.; Zhang, Z.; Lu, X. Organometallics 2000, 19, 775. (b) Zhang, Z.; Lu, X.; Xu, Z.; Zhang, Q.; Han, X. Organometallics 2001, 20, 3724.
35. In the Pd(II)-catalyzed coupling reactions, the halide ion can block the β-H elimination of a carbon-palladium bond, giving preferentially the protonolysis or β-heteroatom elimination product, see: (a) Wang, Z.; Zhang, Z.; Lu, X. Organometallics 2000, 19, 775. (b) Zhang, Z.; Lu, X.; Xu, Z.; Zhang, Q.; Han, X. Organometallics 2001, 20, 3724.
36. (a) Lu, X.; Zhu, G.; Ma, S. Tetrahedron Lett. 1992, 33, 7205.
37. (b) Wakabayashi, T.; Ishii, Y.; Murata, T.; Mizobe, Y.; Hidai, M. Tetrahedron Lett. 1995, 36, 5585.
38. (a) House, H. O. Modern Synthetic Reactions, 2nd ed.; Benjamin: London, UK, 1972; p 313.
39. (b) Nogradi, M. In Stereoselective Synthesis; Verlag Chemie: Weinheim, Germany, 1987; p 193.
40. (c) Evans, D. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: Orlando, FL, 1984; Vol. 3, p 119.
41. (a) Zhang, Q.; Lu, X. J. Am. Chem. Soc. 2000, 122, 7604.
42. (b) Zhang, Q.; Lu, X.; Han, X. J. Org. Chem. 2001, 66, 7676.
43. (a) Trost, B. M.; Sorum, M. T.; Chan, C.; Harms, A. E.; Rühter, G. J. Am. Chem. Soc. 1997, 119, 698.
44. (b) Melikyan, G. G.; Nicholas, K. M. In Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; VCH: New York, 1995; p 79.
45. (a) Mahrwald, R.; Schick, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 593.
46. (b) Ono, M.; Itoh, I. Tetrahedron Lett. 1989, 30, 207.
47. (c) Yakemoto, T.; Nishikimi, Y.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1992, 33, 3527.