A one-pot, stereoselective synthesis of (Z)-1,2-disubstituted vinyl sulfides by sequential hydrostannylation and Stille reaction of acetylenic sulfides with tributyltin hydride and then with aryl iodides

Journal of Chemical Research

Volumn , Issue 7, 2007, Pages 418-419

  Hao, Wenyan ^a   Wang, Dong ^a   Cai, Mingzhong ^a  

^a JIANGXI NORMAL UNIVERSITY   (China)

Author keywords

(Z) 1,2 Disubstituted vinylsulfide; Acetylenic sulfide; Hydrostannylation; Stereoselective synthesis; Stille coupling

Indexed keywords

EID: 34748917139     PISSN: 03082342     EISSN: None     Source Type: Journal    
DOI: 10.3184/030823407X228777     Document Type: Article

References (14)

1. P.R. Marfat, P. McGuirk and P. Helquist, J. Org. Chem., 1979, 44, 3888.
2. M. Obayashi, K. Utimoto and H. Nozaki, Bull. Chem. Soc. Jpn, 1979, 52, 1760.
3. Y. Masaki, K. Sakuma and K. Kaji, J. Chem. Soc., Chem. Commun., 1980, 434.
4. X. Huang and A.M. Sun, J. Org. Chem., 2000, 65, 6561.
5. H.X. Wei, S.H. Kim, T.D. Caputo, D.W. Purkiss and G.G. Li, Tetrahedron, 2000, 56, 2397.
6. (a) T.Y. Luh and Z.J. Ni, Synthesis, 1990, 89;
7. (b) E. Wenkert, T.W. Ferreira and E.L. Michelotti, J. Chem. Soc., Chem. Commun., 1979, 637;
8. (c) V. Fiandanese, G. Marchese, F. Naso and L. Ronzini, J. Chem. Soc., Perkin Trans. 1, 1985, 1115.
9. B.M. Trost and C.J. Li, Synthesis, 1994, 1267.
10. P.A. Magriotis, J.T. Brown, M.E. Scott, Tetrahedron Lett., 1991, 32, 5047.
11. (a) J.K. Stille, Angew. Chem. Int. Ed. Engl., 1986, 25, 508;
12. (b) J.K. Stille and B. L. Groh, J. Am. Chem. Soc., 1987, 109, 813.
13. (c) T.N. Mitchell, Synthesis, 1992, 803.
14. L.M. Venanzi, J. Chem. Soc., 1958, 719.