A novel stereoselective synthesis of (Z)-α-arylsulfanyl-α,β-unsaturated ketones via Stille coupling of (E)-α-arylsulfanylvinylstannanes with acyl halides
Fang Yao
School of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, People's Republic of China
Department of Chemistry and Pharmaceutical Engineering, West Branch of Zhejiang University of Technology, Quzhou 324000, People's Republic of China
Search for more papers by this authorShengyong You
School of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, People's Republic of China
Search for more papers by this authorCorresponding Author
Mingzhong Cai
School of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, People's Republic of China
School of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, People's Republic of ChinaSearch for more papers by this authorFang Yao
School of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, People's Republic of China
Department of Chemistry and Pharmaceutical Engineering, West Branch of Zhejiang University of Technology, Quzhou 324000, People's Republic of China
Search for more papers by this authorShengyong You
School of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, People's Republic of China
Search for more papers by this authorCorresponding Author
Mingzhong Cai
School of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, People's Republic of China
School of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, People's Republic of ChinaSearch for more papers by this authorAbstract
(E)-α-Arylsulfanylvinylstannanes react with acyl halides in the presence of a catalytic amount of Pd(PPh3)4 and CuI cocatalyst to give stereoselectively the corresponding (Z)-α-arylsulfanyl-α,β-unsaturated ketones in good yields. © 2009 Wiley Periodicals, Inc. Heteroatom Chem 20:218–223, 2009; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20536
References
- 1 Nielsen, A. T., Houlihan, W. Org React 1968, 16, 15.
- 2 Chong, B. D., Ji, Y. I., Oh, S. S., Yang, J. D., Baik, W., Koo, S. J Org Chem 1997, 62, 9323.
- 3 Nenitzescu, C. D., Balaban, A. T. Friedel–Crafts Relat React 1964, 3, 1035.
- 4 Carr, D. B., Schwartz, J. J Am Chem Soc 1977, 99, 639.
- 5 Sung, J. W., Jang, W. B., Oh, D. Y. Tetrahedron Lett 1996, 37, 7537.
- 6 Zhao, C. Q., Huang, X. Tetrahedron Lett 1998, 39, 1933.
- 7 Huang, Z. Z., Huang, X., Huang, Y. Z. J Chem Soc, Perkin Trans 1 1995, 95.
- 8 Ma, Y., Li, B., Huang, X. J Organomet Chem 1999, 590, 234.
- 9 Oki, M., Kobayashi, K. Bull Chem Soc Japan 1970, 43, 1223.
- 10
Mukayama, T.,
Hosoi, K.,
Inokuma, S.,
Kumamoto, T.
Bull Chem Soc Japan
1971,
44,
2453.
10.1246/bcsj.44.2453 Google Scholar
- 11 Schultz, A. G., Kashdan, D. S. J Org Chem 1973, 38, 3814.
- 12 Markeley, L. D. J Org Chem 1973, 38, 3417.
- 13 Mukayama, T., Adachi, T., Kumamota, T. Bull Chem Soc Japan 1971, 44, 3155.
- 14 Cregge, R. J., Herrmann, J. L., Schlessinger, R. H. Tetrahedron Lett 1973, 2603.
- 15 Monteiro, H. J., Gemal, A. L. Synthesis 1975, 437.
- 16 Durman, J., Grayson, J. I., Hunt, P. G., Warren, S. J Chem Soc, Perkin Trans 1 1986, 1939.
- 17 Yechezkel, T., Ghera, E., Ostercamp, D., Hassner, A. J Org Chem 1995, 60, 5135.
- 18 Fringuell, F., Pizzo, F., Vaccaro, L. J Org Chem 2004, 69, 2315.
- 19 Xu, F., Shi, W., Wang, J. J Org Chem 2005, 70, 4191.
- 20 Hao, W., Wang, D., Cai, M. J Chem Res 2007, 418.
- 21 Hao, W., Yu, L., Cai, M. J Chem Res 2007, 177.
- 22 Yu, L., Hao, W., Cai, M. Chin Chem Lett 2008, 19, 1047.
- 23 Hu, R., Yu, Y., Cai, M. J Chem Res 2008, 592.
- 24 Zhao, H., Zhang, H., Cai, M. Chin J Chem 2008, 26, 799.
- 25 Trost, B. M., Li, C. J. Synthesis 1994, 1267.
- 26 Magriotis, P. A., Brown, J. T., Scott, M. E. Tetrahedron Lett 1991, 32, 5047.
- 27 Stille, J. K. Angew Chem, Int Ed Engl 1986, 25, 508.
- 28 Mitchell, T. N. J Organomet Chem 1986, 304, 1.
- 29 Cai, M.-Z., Wang, D., Wang, P.-P. J Organomet Chem 2006, 691, 737.
- 30 Liebeskind, L. S., Fengl, R. W. J Org Chem 1990, 55, 5359.
- 31 Linderman, R. J., Siedleck, J. M. J Org Chem 1996, 61, 6492.
- 32 Piers, E., Wong, T. J Org Chem 1993, 58, 3609.
- 33 Falck, J. R., Bhatt, R. K., Ye, J. J Am. Chem Soc 1995, 117, 5973.
- 34 Beletskaya, I. P., Cheprakov, A. V. Coord Chem Rev 2004, 248, 2337.
- 35 Stille, J. K. Pure Appl Chem 1985, 57, 1771.
- 36 Kroehnke, F., Ahrenholz, G. W., Gross, K. F. J Prakt Chem 1960, 11, 256.