Palladium-catalyzed hydroselenation of allenes with benzeneselenol

Tetrahedron Letters

Volumn 39, Issue 29, 1998, Pages 5213-5216

  Ogawa, Akiya ^a   Kudo, Atsuko ^a   Hirao, Toshikazu ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; BENZENE DERIVATIVE; PALLADIUM; SELENIUM DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; SYNTHESIS;

EID: 0032537669     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01024-7     Document Type: Article

References (36)

1. 1. (a) Hiyama, T.; Kusumoto, T. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 8, p 763.
2. (b) Ojima, I. In The Chemistry of Organic Silicon Compounds; Patai, S.; Rappoport, Z., Eds.; John Wiley & Sons: Chichesier, 1989; Part 2, p 1479.
3. (c) Murai, S.; Chatani, N. J. Synth. Org. Chem., Jpn. 1993, 51, 421.
4. 2. (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
5. (b) Mitchell, T. N. Synthesis 1992, 803.
6. (c) Pereyre, M.; Quintard, J. -P.; Rahm, A. Tin in Organic Synthesis; Butterworths: London, 1987.
7. (j) Harrison, P. G. Chemistry of Tin; Blackie & Sons: New York, 1989.
8. 3. (a) Burgess, K.; Ohlmeyer, M. J. Chem. Rev. 1991, 91, 1179.
9. (b) Beletskaya, I.; Pelter, A. Tetrahedron 1997, 53, 4957.
10. (c) Suzuki, A.; Miyaura, N. J. Synth. Org. Chem., Jpn. 1993, 51, 1043.
11. 4. (a) Shier, G. D. J. Organometal. Chem. 1967, 10, 15.
12. (b) Coulson, D. R. J. Org. Chem. 1973, 38, 1483.
13. (c) Cherkezishvili, K. I.; Taktakishvili, M. O.; Gverdtsiteli, I. M. Soobshch. Akad. Nauk Gruz. SSR 1975, 77, 609.
14. 5. (a) Corriu, R. J. P. J. Organometal. Chem. 1972, 40, 73.
15. (b) Ichinose, Y.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1988, 61, 2693.
16. 6. (a) Mitchell, T. N.; Schneider, U. J. Organometal. Chem. 1991, 405, 195.
17. (b) Koerber, K.; Gore, J.; Vatele, J. -M. Tetrahedron Lett. 1991, 32, 1187.
18. (c) Gevorgyan, V.; Liu, J. -X.; Yamamoto, Y. J. Org. Chem. 1997, 62, 2963.
19. (d) Lautens, M.; Ostrovsky, D.; Tao, B. Tetrahedron Lett. 1997, 38, 6343.
20. 7. Ogawa, A.; Kawakami, J.; Sonoda, N.; Hirao, T. J. Org. Chem. 1996, 61, 4161.
21. 8. (a) Ogawa, A.; Kawakami, J.; Mihara, M.; Ikeda, T.; Sonoda, N.; Hirao, T. J. Am. Chem. Soc. 1997, 119, 12380.
22. (b) Ogawa, A.; Kuniyasu, H.; Sonoda, N.; Hirao, T. J. Org. Chem. 1997, 62, 8361.
23. (c) Ogawa, A.; Sonoda, N. J. Synth. Org. Chem., Jpn. 1996, 54, 894.
24. (d) Ogawa, A.; Takeba, M.; Kawakami, J.; Ryu, I.; Kambe, N.; Sonoda, N.J. Am. Chem. Soc. 1995, 117, 7564.
25. (e) Ogawa, A.; Sonoda, N. J. Synth. Org. Chem., Jpn. 1993, 51, 815.
26. (f) Kuniyasu, H.; Ogawa, A.; Sonoda, N. Tetrahedron Lett. 1993, 34, 2491.
27. (g) Kuniyasu, H.; Ogawa, A.; Sato, K.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 5902.
28. (h) Kuniyasu, H.; Ogawa, A.; Higaki, K.; Sonoda, N. Organometallics 1992, 11, 3937.
29. (i) Kuniyasu, H.; Ogawa, A.; Sato, K.; Ryu, I.; Sonoda, N. Tetrahedron Lett. 1992, 33, 5525.
30. (j) Kuniyasu, H.; Ogawa, A.; Miyazaki, S.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1991, 113, 9796.
31. 9. (a) Comasseto, J. V. J. Organomet. Chem. 1983, 253, 131.
32. (b) Comasseto, J. V.; Ling, L. W.; Petragnani, N.; Stefani, H. A. Synthesis 1997, 373.
33. 10. As the ratio of allene/benzeneselenol is decreased, the yield of the vinylic selenide was also decreased and, instead, diphenyl diselenide was obtained as a byproduct: e.g., the yield of 2c = 56% (1c, 1 equiv); 61% (1c, 2 equiv); 69% (1c, 3 equiv); 79% (1c, 5 equiv).
34. 20Se: C, 64.51; H, 7.22. Found: C, 64.22; H, 7.13.
35. 12. Masawaki, T.; Ogawa, A.; Kambe, N.; Ryu, I.; Sonoda, N. Chem. Lett. 1987, 2407.
36. □) and exhibits lower catalytic activity than the real catalyst formed in situ in the catalytic reaction, which probably has a monomeric structure.