Palladium-catalysed hydrostannylation of acetylenic sulfones 1 in benzene at room temperature gives stereoselectively (E)-α-stannylvinyl sulfones 2 in good to high yields. (E)-α-Stannylvinyl sulfones 2 are difunctional group reagents which undergo cross-coupling reactions with alkynyl bromides 3 in the presence of Pd(PPh3)4 and CuI co-catalyst to afford stereoselectively (Z)-2-arylsulfonyl-substituted 1,3-enynes 4 in good yields.
(a) StutzA.Angew. Chem. Int. Ed. Engl, 1987, 26, 320; (b) P. Nussbaumer, L. Leitner, K. Mraz and A. Stutz, J. Med. Chem., 1995, 38, 1831.
2.
MyersA.G., ProteauP.J., and HandelT.M., J. Am. Chem. Soc., 1988, 110, 7212.
3.
(a) AkselaR., and OehlschlagerA.C., Tetrahedron, 1991, 47, 1163; (b) P. Magnus, A. Hirokazo and J. Harling, J. Org. Chem., 1990, 55, 1709; (c) S. Ikeda and Y. Sato, J. Am. Chem. Soc., 1994, 116, 5975; (d) M. Alami, S. Gueugnot, E. Domingues and G. Linstrumelle, Tetrahedron, 1995, 51, 1209; (e) H.A. Stefani, R. Cella, F.A. Dorr, C.M.P. Pereira, G. Zeni and M. Gomes, Tetrahedron Lett., 2005, 46, 563.
4.
(a) MagriotisP.A., and KimK.D., J. Am. Chem. Soc., 1993, 115, 2972; (b) J.A. Miller and G. Zweifel, J. Am. Chem. Soc., 1983, 105, 1383; (c) E.J. Corey and A. Tramontano, J. Am. Chem. Soc., 1984, 106, 462.
5.
HaraR., LiuY., SunW.-H., and TakahashiT., Tetrahedron Lett., 1997, 38, 4103.
6.
CadiernoV., GamasaM.P., and GimenoJ., J. Organomet. Chem., 2001, 621, 39.
7.
(a) KoreedaM., and YangW., Synlett, 1994, 201; (b) M. Cai, D. Wang and P. Wang, J. Chem. Res., 2006, 504.
8.
(a) HuangX., and WangY.P., Tetrahedron Lett., 1996, 37, 7417; (b) M. Cai and J. Chen, J. Chem. Res., 2004, 840.
9.
(a) BragaA.L., ZeniG., AndradeL.H., SilveiraC.C., and StefaniH.A., Synthesis, 1998, 39; (b) Y. Ma and X. Huang, Synth. Commun. 1997, 27, 3441; (c) M.Z. Cai, C.Y. Peng, H. Zhao and J.D. Huang, J. Chem. Res.(S), 2002, 376; (d) P. Zhong and N. Huang, Synth. Commun., 2002, 32, 139.
10.
(a) ChataniN., AmishiroN., and MuraiS., J. Am. Chem. Soc., 1991, 113, 7778; (b) M. Cai, W. Hao, H. Zhao and C. Song, J. Chem. Res.(S), 2003, 485.
11.
(a) HuangX., and ZhongP., J. Chem. Soc., Perkin Trans. 1, 1999, 1543; (b) M. Cai, H. Zhao, H. Ye, J. Xia and C. Song, J. Chem. Res.(S), 2003, 344.
12.
(a) YoshidaM., YoshikawaS., FukuharaT., YonedaN., and HaraS., Tetrahedron, 2001, 57, 7143; (b) J. Legros, B. Crousse, D. Bonnet-Delpon and J.P. Begue, J. Fluor. Chem., 2001, 107, 121.
YoshimatsuM., and HasegawaJ., J. Chem. Soc., Perkin Trans. 1, 1997, 211.
15.
YoshimatsuM., KawahigashiM., ShimizuH., and KataokaT., J. Chem. Soc., Chem. Commun., 1995, 583.
16.
(a) TrostB.M., ChanC., and RuhterG., J. Am. Chem. Soc., 1987, 109, 3486; (b) B.M. Trost, M.T. Sorum, C. Chan, A.E. Harms and G. Ruhter, J.Am. Chem. Soc., 1997, 119, 698.
17.
(a) BragaA.L., ZeniG., de AndradeL.H., SilveiraC.C., and StefaniH.A., Synthesis, 1998, 39; (b) F. Ye, A. Orita, A. Doumoto and J. Otera, Tetrahedron, 2003, 59, 5635; (c) M. Yoshimatsu, S. Gotoh, E. Gotoh, G. Tanabe and O. Muraoka, J. Chem. Soc., Perkin Trans. 1, 1997, 3035; (d) S. Matsumoto, T. Kobayashi, K. Ogura, Heterocycles, 2006, 68, 283.
(a) MagriotisP.A., DoyleT.J., and KimK.D., Tetrahedron Lett., 1990, 31, 2541; (b) J.K. Stille and J.H. Simpson, J. Am. Chem. Soc., 1987, 109, 2138; (c) N. Chatani, N. Amishiro and S. Murai, J. Am. Chem. Soc., 1991, 113, 7778.
20.
(a) LiebeskindL.S., and FenglR.W., J. Org. Chem., 1990, 55, 5359; (b) G.J. Hollingworth and J.B. Sweeney, Synlett, 1993, 463; (c) S.-K. Kang, W.-Y. Kim and X. Jiao, Synthesis, 1998, 1252.
21.
MagriotisP.A., BrownJ.T., and ScottM.E., Tetrahedron Lett., 1991, 32, 5047.
22.
HuangX., and MaY., Synth. Commun., 1997, 27, 2407.
23.
PaleyR.S., WeersH.L., and FernandezP., Tetrahedron Lett., 1995, 36, 3605.
24.
XiangJ.S., MahadevanA., and FuchsP.L., J. Am. Chem. Soc., 1996, 118, 4284.
25.
(a) BoothC., ImaniehH., QuayleP., and Shui-YuL., Tetrahedron Lett., 1992, 33, 413; (b) M. Pohmakotr and S. Khosavanna, Tetrahedron, 1993, 49, 6483; (c) E. Shirakawa, H. Yoshida, Y. Nakao and T. Hiyama, Org. Lett., 2000, 2, 2209; (d) D. Modec and J.-P. Ferezou, Eur. J. Org. Chem., 2006, 92.
26.
LeusinkA.J., BuddingH.A., and MarsmanJ.W., J. Organomet. Chem., 1967, 9, 285.
