Sequential one-pot reactions of thioformates with lithium silylacetylides, arylmagnesium halides, and electrophiles leading to formation of propargyl sulfides

Chemistry Letters

Volumn 40, Issue 1, 2011, Pages 70-71

  Murai, Toshiaki ^a   Ohashi, Takayuki ^a   Shibahara, Fumitoshi ^a  

^a GIFU UNIVERSITY   (Japan)

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EID: 78751515654     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.2011.70     Document Type: Review

References (31)

1. For reviews, see: a) A. Inoue, K. Oshima, in Main Group Metals in Organic Synthesis, ed. by H. Yamamoto, K. Oshima, Wiley-VCH, Weinheim, 2004, Vol. 1, p. 51.
2. P. Knochel, A. Krasovskiy, I. Sapountzis, in Handbook of Functionalized Organometallics, ed. by P. Knochel, Wiley-VCH, Weinheim, 2005, Vol. 1, p. 109.
3. a) L. Miginiac, in Handbook of Grignard Reagents, ed. by G. S. Silverman, P. E. Rakita, Marcel Dekker, New York, 1996, p. 364.
4. B. J. Wakefield, in Organomagnesium Methods in Organic Synthesis, Academic Press, London, UK, 1995, pp. 147, 209.
5. P. Metzner, Organosulfur Chemistry I in Topics in Current Chemistry, ed. by P. C. B. Page, Springer-Verlag, Berlin, 1999, Vol. 204, p. 127. doi:10.1007/3-540-48956-8-2
6. a) P. Beak, J. W. Worley, J. Am. Chem. Soc. 1970, 92, 4142.
7. P. Beak, J. W. Worley, J. Am. Chem. Soc. 1972, 94, 597.
8. A. Ishii, T. Ishida, N. Kumon, N. Fukuda, H. Oyama, N. Inamoto, F. Iwasaki, R. Okazaki, Bull. Chem. Soc. Jpn. 1996, 69, 709.
9. For recent examples, see: a) V. V. Kouznetsov, L. Y. V. Méndez, Synthesis 2008, 491.
10. M. B. Boxer, H. Yamamoto, Org. Lett. 2008, 10, 453.
11. A. Agosti, S. Britto, P. Renaud, Org. Lett. 2008, 10, 1417.
12. O. Tomashenko, V. Sokolov, A. Tomashevskiy, H. A. Buchholz, U. Welz-Biermann, V. Chaplinski, A. de Meijere, Eur. J. Org. Chem. 2008, 5107.
13. E. Yoshioka, S. Kohtani, H. Miyake, Org. Lett. 2010, 12, 1956.
14. K.-J. Xiao, J.-M. Luo, K.-Y. Ye, Y. Wang, P.-Q. Huang, Angew. Chem., Int. Ed. 2010, 49, 3037.
15. S. Suga, D. Yamada, J. Yoshida, Chem. Lett. 2010, 39, 404.
16. T. Murai, Y. Mutoh, Y. Ohta, M. Murakami, J. Am. Chem. Soc. 2004, 126, 5968.
17. T. Murai, F. Asai, J. Am. Chem. Soc. 2007, 129, 780.
18. Thioform esters 1 were prepared by the thionation of the corresponding esters with Lawesson's reagent.
19. For synthesis of 4a, see: a) T. Kondo, Y. Kanda, A. Baba, K. Fukuda, A. Nakamura, K. Wada, Y. Morisaki, T. Mitsudo, J. Am. Chem. Soc. 2002, 124, 12960.
20. J. P. Bacci, K. L. Greenman, D. L. Van Vranken, J. Org. Chem. 2003, 68, 4955.
21. C. Bonini, L. Chiummiento, V. Videtta, Synlett 2005, 3067.
22. The use of 4-methoxy-and 4-(dimethylamino) phenylmagnesium bromides gave the corresponding propargyl sulfides in 67 and 69% yields, whereas the reaction of 4-chlorophenylmagnesium bromide was less efficient.
23. a) G. A. Krafft, P. T. Meinke, Tetrahedron Lett. 1985, 26, 1947.
24. E. Vedejs, T. H. Eberlein, D. J. Mazur, C. K. McClure, D. A. Perry, R. Ruggeri, E. Schwartz, J. S. Stults, D. L. Varie, R. G. Wilde, S. Wittenberger, J. Org. Chem. 1986, 51, 1556.
25. K. Okuma, Y. Tachibana, J. Sakata, T. Komiya, I. Kaneko, Y. Komiya, Y. Yamasaki, S. Yamamoto, H. Ohta, Bull. Chem. Soc. Jpn. 1988, 61, 4323.
26. H. Shinokubo, H. Miki, T. Yokoo, K. Oshima, K. Utimoto, Tetrahedron 1995, 51, 11681.
27. E. Abele, M. Veveris, R. Abele, K. Rubina, P. Arsenyan, D. Meirena, Main Group Met. Chem. 2006, 29, 215.
28. a) A. Armstrong, R. S. Cooke, S. E. Shanahan, Org. Biomol. Chem. 2003, 1, 3142.
29. K. Frimpong, J. Wzorek, C. Lawlor, K. Spencer, T. Mitzel, J. Org. Chem. 2009, 74, 5861.
30. T. Sugimura, K. Hagiya, Chem. Lett. 2007, 36, 566.
31. Supporting Information is available electronically on the CSJ-Journal We b s ite, http://www.csj.jp/journals/chem-lett/index.html.