First ruthenium-catalyzed allylation of thiols enables the general synthesis of allylic sulfides [7]

Journal of the American Chemical Society

Volumn 121, Issue 37, 1999, Pages 8657-8658

  Kondo, Teruyuki ^a   Morisaki, Yasuhiro ^a   Uenoyama, Shin Ya ^a   Wada, Kenji ^a   Mitsudo, Take Aki ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; ALLYL SULFIDE; RUTHENIUM; THIOL DERIVATIVE;

CATALYSIS; CHEMICAL REACTION; LETTER; REACTION ANALYSIS; STEREOCHEMISTRY; STOICHIOMETRY; SYNTHESIS;

EID: 0033595506     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja991704f     Document Type: Letter

References (40)

1. Harrington, P. J. Transition Metals in Total Synthesis; John Wiley & Sons: New York, 1990; p 25.
2. For a review of palladium-catalyzed allylic alkylation, see: (a) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (b) Tsuji, J. Palladium Reagents and Catalysts; John Wiley & Sons: New York, 1995; p 290. (c) Harrington, P. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K., 1995; Vol. 12, p 797.
3. For a review of palladium-catalyzed allylic alkylation, see: (a) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (b) Tsuji, J. Palladium Reagents and Catalysts; John Wiley & Sons: New York, 1995; p 290. (c) Harrington, P. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K., 1995; Vol. 12, p 797.
4. For a review of palladium-catalyzed allylic alkylation, see: (a) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (b) Tsuji, J. Palladium Reagents and Catalysts; John Wiley & Sons: New York, 1995; p 290. (c) Harrington, P. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K., 1995; Vol. 12, p 797.
5. (a) Fe: Enders, D.; Jandeleit, B.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 1949; Angew. Chem. 1994, 106, 2033.
6. (a) Fe: Enders, D.; Jandeleit, B.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 1949; Angew. Chem. 1994, 106, 2033.
7. (b) Co: Bhatia, B.; Reddy, M. M.; Iqbal, J. Tetrahedron Lett. 1993, 34, 6301.
8. (c) Ni: Bricout, H.; Carpentier, J.-F.; Mortreux, A. J. Chem. Soc., Chem. Commun. 1995, 1863.
9. (d) Rh: Evans, P. A.; Nelson, J. D. J. Am. Chem. Soc. 1998, 120, 5581.
10. (e) Ir: Takeuchi, R.; Kashio, M. J. Am. Chem. Soc. 1998, 120, 8647.
11. (f) Pt: Brown, J. M.; MacIntyre, J. E. J. Chem. Soc., Perkin Trans. 2 1985, 961.
12. (g) Mo: Trost, B. M.; Hachiya, I. J. Am. Chem. Soc. 1998, 120, 1104.
13. (h) W: Lloyd-Jones, G. C.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 462; Angew. Chem. 1995, 107, 534 and pertinent references therein.
14. (h) W: Lloyd-Jones, G. C.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 462; Angew. Chem. 1995, 107, 534 and pertinent references therein.
15. (a) Hegedus, L. L.; McCabe, R. W. Catalyst Poisoning; Marcel Dekker: New York, 1984.
16. (b) Hutton, A. T. In Comprehensive Coordination Chemistry; Wilkinson, G., Gillard, R. D., McCleverty, J. A., Eds.; Pergamon: Oxford, U.K., 1984; Vol. 5, p 1151.
17. (a) Yamada, Y.; Mukai, K.; Yoshioka, H.; Tamaru, Y.; Yoshida, Z. Tetrahedron Lett. 1979, 5015.
18. (b) Tamaru, Y.; Yoshida, Z.; Yamada, Y.; Mukai, K.; Yoshioka, H. J. Org. Chem. 1983, 48, 1293.
19. (a) Auburn, P. R.; Whelan, J.; Bosnich, B. J. Chem. Soc., Chem. Commun. 1986, 146.
20. (b) Lu, X.; Ni, Z. Synthesis 1987, 66.
21. Trost, B. M.; Scanlan, T. S. Tetrahedron Lett. 1986, 27, 4141.
22. (a) Moreno-Mañas, M.; Pleixats, R.; Villarroya, M. Tetrahedron 1993, 49, 1457.
23. (b) Arredondo, Y.; Moreno-Manas, M.; Pleixats, R.; Villarroya, M. Tetrahedron 1993, 49, 1465.
24. Kang, S.-K.; Park, D.-C; Jeon, J.-H.; Rho, H.-S.; Yu, C.-M. Tetrahedron Lett. 1994, 35, 2357.
25. (a) Goux, C.; Lhoste, P.; Sinou, D. Tetrahedron Lett. 1992, 33, 8099.
26. (b) Goux, C.; Lhoste, P.; Sinou, D. Tetrahedron 1994, 50, 10321.
27. (c) Genêt, J. P.; Blart, E.; Savignac, M.; Lemeune, S.; Lemaire-Audoire, S.; Bernard, J. M. Synlett 1993, 680.
28. (a) Zhang, S.-W.; Mitsudo, T.; Kondo, T.; Watanabe, Y. J. Organomet. Chem. 1993, 450, 197.
29. (b) Kondo, T.; Ono, H.; Satake, N.; Mitsudo, T.; Watanabe, Y. Organometallics 1995, 14, 1945.
30. (a) Fujita, K.; Ikeda, M.; Kondo, T.; Mitsudo, T. Chem. Lett. 1997, 57.
31. (b) Fujita, K.; Ikeda, M.; Nakano, Y.; Kondo, T.; Mitsudo, T. J. Chem. Soc., Dalton Trans. 1998, 2907.
32. Kondo, T.; Uenoyama, S.; Fujita, K.; Mitsudo, T. J. Am. Chem. Soc. 1999, 121, 482.
33. (a) Luh, T.-Y.; Ni, Z.-J. Synthesis 1990, 89.
34. (b) Planas, J. G.; Hirano, M.; Komiya, S. Chem. Lett. 1998, 123.
35. Bergbreiter, D. E.; Weatherford, D. A. J. Chem. Soc., Chem. Commun. 1989, 883.
36. 3 and dppb reported by Sinou and co-workers (refs 10a,b) in THF at 60 °C for 12 h gave allyl pentyl sulfide (3a) in only 35% yield.
37. For a mechanism with double inversion of configuration in palladiumcatalyzed allylation reactions, see: (a) Hayashi, T.; Yamamoto, A.; Hagihara, T. J. Org. Chem. 1986, 51, 723. (b) Fiaud, J.-C; Legros, J.-Y. J. Org. Chem. 1987, 52, 1907.
38. For a mechanism with double inversion of configuration in palladiumcatalyzed allylation reactions, see: (a) Hayashi, T.; Yamamoto, A.; Hagihara, T. J. Org. Chem. 1986, 51, 723. (b) Fiaud, J.-C; Legros, J.-Y. J. Org. Chem. 1987, 52, 1907.
39. Spera, M. L.; Chin, R. M.; Winemiller, M. D.; Lopez, K. W.; Sabat, M.; Harman, W. D. Organometallics 1996, 15, 5447.
40. Metzner, P.; Thuillier, A. In Sulfur Reagents in Organic Synthesis; Academic Press: London, U.K., 1994; p 75.