Palladium catalyzed hydrosulfination of allenes with tosylhydrazine leading to allylsulfones

Tetrahedron Letters

Volumn 39, Issue 7, 1998, Pages 691-694

  Kamijo, Shin ^a   Al Masum, Mohammad ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; HYDRAZINE DERIVATIVE; PALLADIUM; SULFONE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION;

EID: 0032509936     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10637-2     Document Type: Article

References (21)

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3. (c) Yamamoto, Y.; Al-Masum, M. Synlett 1995, 969-970.
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5. (e) Yamamoto, Y.; Al-Masum, M.; Fujiwara, N. J. Chem. Soc., Chem. Commun. 1996, 381-382.
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7. (g) Al-Masum, M.; Meguro, M.; Yamamoto, Y. Tetrahedron Lett. 1997, 38, 6071-6074.
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11. 2. For 1,3-dienes, see: (a) Trost, B. M.; Zhi, L. Tetrahedron Lett. 1992, 33, 1831-1834.
12. (b) Armbruster, R. W.; Morgan, M. M.; Schmidt, J. L.; Lau, C. M.; Riley, R. M.; Zabrowski, D. L.; Dieck, H. A. Organometallics 1986, 5, 234-237.
13. (c) Rose, D.; Lepper, H.J. Organomet. Chem. 1973, 49, 473-476.
14. (d) Julia, M.; Nel, M.; Saussine, L. J. Organomet. Chem. 1979, 181, C17-C20.
15. 3. For enynes, see: (a) Salter, M. M.; Gevorgyan, V.; Saito, S.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1996, 17-18.
16. (b) Bäckvall, Jan-E.; Ericsson, A. J. Org. Chem. 1994, 59, 5850-5851.
17. 4. For methylenecyclopropanes, see: (a) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123-8124.
18. (b) Bessmertnykh, A. G.; Blinov, K. A.; Grishin, Y. K.; Donskaya, N. A.; Tveritinova, E. V.; Yur'eva, N. M.; Beletskaya, I. P. J. Org. Chem. 1997, 62, 6069-6076.
19. 5. For a review, see: Dzhemilev, U. M.; Kunakova, R. V. J. Organomet. Chem. 1993, 455, 1-27 and references cited therein.
20. 6. The reaction of intermediate C (R = Ph) under the same reaction condition as in eq 1 gave 2a in 57% yield. Further, the reaction of intermediate C with t-butylallene 1e gave 2a and 2e in 26% and 51% yield, respectively.
21. 7. See: ref. 1g.