A facile stereospecific synthesis of 1,3-enynylsulfides via Sonogashira coupling of (E)-α-iodovinyl sulfides with 1-alkynes

Chinese Chemical Letters

Volumn 17, Issue 6, 2006, Pages 757-760

  Jiang, Jian Wen ^a   Cai, Ming Zhong ^a  

^a JIANGXI NORMAL UNIVERSITY   (China)

Author keywords

(E) Iodovinyl sulfide; 1, 3 enynylsulfide; Sonogashira coupling; Terminal alkyne

Indexed keywords

EID: 33745491472     PISSN: 10018417     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (32)

1. (a) A. Stutz, Angew. Chem. Int. Ed. Engl., 1987, 26, 320.
2. (b) P. Nussbaumer, L. Leitner, K. Mraz, A. Stutz, J. Med. Chem., 1995, 38, 1831.
3. A. G. Myers, P. J. Proteau, T. M. Handel, J. Am. Chem. Soc., 1988, 110, 7212.
4. (a) R. Aksela, A. C. Oehlschlager, Tetrahedron, 1991, 47, 1163.
5. (b) P. Magnus, A. Hirokazo, J. Harling, J. Org. Chem., 1990, 55, 1709.
6. (c) S. Ikeda, Y. Sato, J. Am. Chem. Soc., 1994, 116, 5975.
7. (d) M. Alami, S. Gueugnot, E. Domingues, G. Linstrumelle, Tetrahedron, 1995, 51, 1209.
8. (e) H. A. Stefani, R. Cella, F. A. Dorr, et al., Tetrahedron Lett., 2005, 46, 563.
9. (f) M. Feuerstein, L. Chanen, H. Doucet, M. Santelli, Tetrahedron, 2005, in press.
10. (a) P. A. Magriotis, K. D. Kim, J. Am. Chem. Soc., 1993, 115, 2972.
11. (b) J. A. Miller, G. Zweifel, J. Am. Chem. Soc., 1983, 105, 1383.
12. (c) E. J. Corey, A. Tramontano, J. Am. Chem. Soc., 1984, 106, 462.
13. R. Hara, Y. Liu, W. H. Sun, T. Takahashi, Tetrahedron Lett., 1997, 38, 4103.
14. V. Cadierno, M. P. Gamasa, J. Gimeno, J. Organomet. Chem., 2001, 621, 39.
15. (a) X. Huang, Y. P. Wang, Tetrahedron Lett., 1996, 37, 7417.
16. (b) M. Cai, J. Chen, J. Chem. Res., 2004, 840.
17. (a) A. L. Braga, G. Zeni, L. H. Andrade, C. C. Silveira, H. A. Stefani, Synthesis, 1998, 39.
18. (b) Y. Ma, X. Huang, Synth. Commun., 1997, 27, 3441.
19. (c) M. Z. Cai, C. Y. Peng, H. Zhao, J. D. Huang, J. Chem. Res., 2002, 376.
20. (d) P. Zhong, N. Huang, Synth. Commun., 2002, 32, 139.
21. (a) N. Chatani, N. Amishiro, S. Murai, J. Am. Chem. Soc., 1991, 113, 7778.
22. (b) M. Cai, W. Hao, H. Zhao, C. Song, J. Chem. Res., 2003, 485.
23. (a) X. Huang, P. Zhong, J. Chem. Soc., Perkin Trans. 1, 1999, 1543.
24. (b) M. Cai, H. Zhao, H. Ye, J. Xia, C. Song, J. Chem. Res., 2003, 344.
25. (a) M. Yoshida, S. Yoshikawa, T. Fukuhara, N. Yoneda, S. Hara, Tetrahedron, 2001, 57, 7143.
26. (b) J. Legros, B. Crousse, D. Bonnet-Delpon, J. P. Begue, J. Fluor. Chem., 2001, 107, 121.
27. M. Koreeda, W. Yang, Synlett, 1994, 201.
28. (a) A. Suzuki, Pure Appl. Chem., 1985, 57, 1749.
29. (b) T. N. Mitchell, Synthesis, 1992, 803.
30. (a) K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett., 1975, 4467.
31. (b) M. Alami, G. Linstrumelle, Tetrahedron Lett., 1991, 32, 6109.
32. M. Su, W. Yu, Z. Jin, Tetrahedron Lett., 2001, 42, 3771.