Stereoselective synthesis of 1,3-enynylstannanes via palladium catalyzed cross-coupling reactions of (Z)-α-bromovinylstannanes
Ming-Zhong Cai
Institute of Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330027, China
Search for more papers by this authorRong-Li Zhang
Institute of Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330027, China
Search for more papers by this authorHong Zhao
Institute of Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330027, China
Search for more papers by this authorMing-Zhong Cai
Institute of Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330027, China
Search for more papers by this authorRong-Li Zhang
Institute of Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330027, China
Search for more papers by this authorHong Zhao
Institute of Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330027, China
Search for more papers by this authorAbstract
Based on the different reactivity of stannyl and bromo groups, (Z)-α-bromovinylstannanes can undergo the cross-coupling reaction with alkynyl Grignard reagents in the presence of tetrakis(triphenylphosphine)palladium(O) catalyst in THF at room temperature to afford stereoselectively 1,3-enynylstannanes in good yields.
References
- 1(a) Magnus, P.; Hirokazo, A.; Haling, J. J. Org. Chem. 1990, 55, 1709. (b) Aksela, R.; Oehlschlager, A. C. Tetrahedron 1991, 47, 1163. (c) Ikeda, S.; Sato, Y. J. Am. Chem. Soc. 1994, 116, 5975. (d) Alami, M.; Gueugnot, S.; Domingues, E.; Linstrumelle, G. Tetrahedron 1995, 51, 1209. (e) Yoshimatsu, M.; Hayashi, M.; Tanabe, G.; Muraoka, O. Tetrahedron Lett. 1996, 37, 4161.
- 2 Magriotis, P. A.; Kim, K. D. J. Am. Chem. Soc. 1993, 115, 2912.
- 3(a) Miller, J. A.; Zweifel, G. J. Am. Chem. Soc. 1983, 105, 1383. (b) Corey, E. J.; Tramontano, A. J. Am. Chem. Soc. 1984, 106, 462.
- 4(a) Stuutz, A. Angew. Chem., Int. Ed. Engl. 1987, 26, 320. (b) Nussbaumer, P.; Leitner, L.; Mraz, K.; Stutz, A. J. Med. Chem. 1995, 38, 1831.
- 5(a) Lee, M. D.; Dunne, T. S.; Chang, C. C.; Ellestad, G. A.; Siegel, M. M.; Morton, G. O.; McGahren, W. J.; Borders, D. B. J. Am. Chem. Soc. 1987, 109, 3466. (b) Myers, A. G.; Proteau, P. J.; Handel, T. M. J. Am. Chem. Soc. 1988, 110, 7212.
- 6(a) Dabdoub, M. J.; Dabdoub, V.; Comasseto, J. V. Tetrahedron Lett. 1992, 33, 2261. (b) Marino, J. P.; Tucci, F.; Comasseto, J. V. Synlett 1993, 761.
- 7 Koreeda, M.; Yang, W. Synlett 1994, 201.
- 8 Babudri, F.; Fiandanese, V.; Mazzone, L.; Naso, F. Tetrahedron Lett. 1994, 35, 8847.
- 9 Magriotis, P. A.; Doyle, T. J.; Kim, K. D. Tetrahedron Lett. 1990, 31, 2541.
- 10(a) Braga, A. L.; Zeni, G.; Andrade, L. H.; Silveira, C. C.; Stefani, H. A. Synthesis 1998, 39. (b) Huang, X.; Wang, Y. P. Symth. Commun. 1996, 26, 3087.
- 11 Ma, Y.; Huang, X. Synth. Commun 1997, 27, 3441.
- 12(a) Chatani, N.; Amishiro, N.; Murai, S. J. Am. Chem. Soc. 1991, 113, 1118. (b) Cai, M.; Hao, W.; Zhao, H.; Song, C. J. Chem. Res. 2003, 485.
- 13 Huang, X.; Bong, P. J. Chem Soc., Perkin Trans. 1 1999, 1543.
- 14 Lipshuts, B. H.; Keil, R.; Barton, J. C. Tetrahedron Lett. 1992, 33, 5861.
- 15(a) Grobel, B. T.; Seebach, D. Chem Ber. 1977, 110, 867. (b) Pelter, A.; Smith, K.; Parry, D. E.; Jones, K. D. Aust. J. Chem. 1992, 45, 57.
- 16 Schwartz, J.; Labinger, I. A. Angew. Chem, Int. Ed Engl. 1976, 15, 333.
- 17 Logue, M. W.; Teng, K. J. Org. Chem 1982, 47, 2549.
- 18 Coulson, D. R. Inorg. Synth. 1972, 13, 121.
- 19 Marcuzzi, F.; Azzena, U.; Melloni, G. J. Chem Soc., Perkin Trans. 1 1993, 2951.
