Highly Regioselective Palladium-Catalyzed Thiocarbonylation of Allenes with Thiols and Carbon Monoxide

Journal of Organic Chemistry

Volumn 63, Issue 8, 1998, Pages 2609-2612

  Xiao, Wen Jing ^a   Vasapollo, Giuseppe ^a,b   Alper, Howard ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

^b UNIVERSITY OF SALENTO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001243872     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo972121w     Document Type: Article

References (40)

1. (a) Dubois, M. R. Chem. Rev. 1989, 89, 1.
2. (b) Hegedus, L. L.; McCabe, R. W. Catalyst Poisoning; Marcel Dekker: New York, 1984.
3. Hutton, A. T. In Comprehensive Coordination Chemistry; Wilkinson, G., Gillard, R. D., McCleverty, J. A., Eds.; Pergamon Press: Oxford, U.K., 1984; Vol. 5, p 1151.
4. (a) Frost, C. G.; Williams, J. M. J. Tetrahedron Lett. 1993, 34, 2015.
5. (b) Yamamoto, T.; Sekine, Y. Inorg. Chim. Acta 1984, 83, 47.
6. Canich, J. M.; Cotton, F. A.; Dunbar, K. R.; Falvello, L. R. Inorg. Chem. 1988, 27, 804.
7. Murray, S. G.; Hartley, F. R. Chem. Rev. 1981, 81, 365.
8. (a) Antebi, S.; Alper, H. Organometallics 1986, 5, 596.
9. (b) Shim, S. C.; Antebi, S.; Alper, H. J. Org. Chem. 1985, 50, 147.
10. Shim, S. C.; Antebi, S.; Alper, H. Tetrahedron Lett. 1985, 26, 1935.
11. Wand, M. D.; Calet, S.; Alper, H. J. Org. Chem. 1989, 54, 20.
12. (e) Antebi, S.; Alper, H. Can. J. Chem. 1986, 64, 2010.
13. (f) Calet, S.; Alper, H. Organometallics 1987, 6, 1625.
14. (g) Calet, S.; Alper, H. Tetrahedron Lett. 1986, 27, 3573.
15. (h) Antebi, S.; Alper, H. Tetrahedron Lett. 1985, 26, 2609.
16. Crudden, C. M.; Alper, H. J. Org. Chem. 1995, 60, 5579.
17. (j) Xiao, W.-J.; Alper, H. J. Org. Chem. 1997, 62, 3422.
18. (k) Ogawa, A.; Takeba, M.; Kawakami, J.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1995, 117, 7564.
19. Ogawa, A.; Kawakami, J.; Sonoda, N.; Hirao, T. J. Org. Chem. 1996, 61, 4161.
20. Luh, T. Y.; Ni, Z. J. Synthesis 1990, 89.
21. (n) Goux, C.; Lhoste, P.; Sinon, D. Tetrahedron Lett. 1992, 33, 8099.
22. (o) Kuniyasu, H.; Ogawa, A.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 5902.
23. (p) Kuniyasu, H.; Ogawa, A.; Miyazaki, S.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1991, 113, 9796.
24. (q) Keim, W.; Herwig, J. J. Chem. Soc., Chem. Commun. 1993, 1592.
25. (r) Khumtaveeporn, K.; Alper, H. J. Org. Chem. 1994, 59, 1414.
26. (B) Backvall, J. E.; Ericsson, A. J. Org. Chem. 1994, 59, 5850.
27. (a) Khumtaveeporn, K.; Alper, H. J. Chem. Soc., Chem. Commun. 1995, 917.
28. (b) Okamura, H.; Miura, M.; Takei, H. Tetrahedron Lett. 1979, 43.
29. Grushin, V. V. Chem. Rev. 1996, 96, 2011.
30. 2.
31. Tsuji, J. Palladium Reagents and Catalysts; John Wiley & Sons: New York, 1995.
32. (a) Merz, A. Angew. Chem., Int. Ed. Engl. 1973, 12, 846.
33. (b) Meyer, A.; McCabe, D. J.; Curtis, M. D. Organometallics 1987, 6, 1491.
34. Skattebol, L.; Solomon, S. Organic Syntheses; Wiley: New York, 1973; Collect. Vol. V, p 306.
35. Crabbe, P.; Nassim, B.; Robert-Lopes, M.-T. Organic Syneses; Wiley: New York, 1990; Collect. Vol. VI, p 276.
36. Lang, R. W.; Hansen, H.-J. Helv. Chim. Acta 1980, 63, 438.
37. (a) Bach, R. D.; Mazur, U.; Brummel, R. N.; Lin, L.-H. J. Am. Chem. Soc. 1971, 93, 7120.
38. (b) Okude, Y.; Hiyama, T.; Nozaki, H. Tetrahedron Lett. 1977, 43, 3829.
39. Ukai, T.; Kawazura, H.; Shii, Y. J. Organomet. Chem. 1974, 65, 253.
40. Cramer, R. Inorg. Synth. 1974, 15, 14.