The aim of this work is to study the influence of the nature and position of substitution at allyl benzene on the regioselectivity of the hydrosilylation reaction. We studied hydrosilylation of the various allyl derivatives with cyclic siloxane, D4H, and linears hydrosilylating agents, 1,1,3,3-tetramethyldisiloxane and MDHM, in the presence of platinum-based catalysts (Karstedt catalyst, platinum black). We also show the effects of the amount of catalyst on the conversion. Moreover, the influence on the temperature on catalytic activity and selectivity of the hydrosilylation reaction was explained. All new compounds were characterized by 1H, 13C, 29Si NMR and HRMS as well.
Cite this paper
Rbihi, Z. , Lanaya, S. E. , Guida, M. Y. , Rakib, E. M. , Barakat, A. , Malki, A. E. and Hannioui, A. (2021). β-Hydrosilylation of Allylic Derivatives with Cyclic and Linear Siloxanes in the Presence of Platinum Catalysts. Open Access Library Journal, 8, e7364. doi: http://dx.doi.org/10.4236/oalib.1107364.
Kendrick, T.C., Parbhoo, B. and White, J.W. (1989) Chemistry of Organic Silicon Compounds. In: Patai, S. and Rappaport, Z., Eds., Chapter 21, John Wiley & Sons, Chichester.
Saam, J.C. (1990) In Silicon Based Polymer Science. In: Zeigler, J.M. and Gordon Fearon, F.W., Eds., Advances in Chemistry Series 224, American Chemical Society, Washington, DC.
Ryan, J.W. and Speier, L. (1964) The Addition of Silicon Hydrides to Olefinic Double Bonds. VIII. The Addition of Trichlorosilane-d. Journal of the American Chemical Society, 86, 895-898.
Speier, J.L., Webster, J.A. and Barnes, G.H. (1957) The Addition of Silicon Hydrides to Olefinic Double Bonds. Part II. The Use of Group VIII Metal Catalysts. Journal of the American Chemical Society, 79, 974-979. https://doi.org/10.1021/ja01561a054
Lewis, L.N. and Lewis, N.J. (1986) Platinum-Catalyzed Hydrosilylation Colloid Formation as the Essential Step. Journal of the American Chemical Society, 108, 7228. https://doi.org/10.1021/ja00283a016
Zhang, C.R. and Laine, M.J. (2000) Hydrosilylation of Allyl Alcohol with [HSiMe2OSiO1.5]8: Octa(3-Hydroxypropyldimethylsiloxy)octasilsesquioxane and Its Octamethacrylate Derivative as Potential Precursors to Hybrid Nanocomposites. Journal of the American Chemical Society 122, 6979-6988.
https://doi.org/10.1021/ja000318r
El Malki, Hannioui, A., Rakib, E.M., Knouzi, N. and Vaultier, M. (2011) Regioselective Platinum Catalyzed-Hydrosilylation of Allylic Benzene Derivatives with Cyclic Siloxane D4H. Letters in Organic Chemistry, 8, 361-363.
https://doi.org/10.2174/157017811795684992
Igarashi, M., Matsumoto, T., Kobayashi, T., Sato, K., Ando, W., Shimada, S., Hara, M. and Uchida, H. (2014) Hydrosilylation of Allyl Derivatives with T, D and M Type Hydrosilanes. Journal of Organometallic Chemistry, 749, 421-427.
https://doi.org/10.1016/j.jorganchem.2013.10.014
Yang, X.L., Bai, Y., Li, J.Y., Dai, Z.N. and Peng, J.J. (2019) Hydrosilylation of Alkenes Catalyzed by Fe Powder. Phosphorus, Sulfur, and Silicon and the Related Elements, 194, 1-4. https://doi.org/10.1080/10426507.2018.1506782