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Categories: C-Si Bond Formation > Silanes

Synthesis of benzylsilanes

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A Ni/Cu-catalyzed silylation of unactivated C-O electrophiles derived from phenols or benzyl alcohols offers a wide scope and mild conditions and provides a direct access to synthetically versatile silylated compounds.
C. Zarate, R. Martin, J. Am. Chem. Soc., 2014, 136, 2236-2239.


A cobalt-catalyzed enantioselective hydrosilylation of terminal alkenes enables an efficient synthesis of valuable chiral dihydrosilanes. This protocol is operationally simple and atom-economic using relatively simple and readily available starting materials.
B. Cheng, P. Lu, H. Zhang, X. Cheng, Z. Lu, J. Am. Chem. Soc., 2017, 139, 9439-9442.


A novel catalytic system for the asymmetric hydrosilylation of aromatic alkenes is described, which leads to silanes in high yields and with excellent enantioselectivity. The reaction works efficiently for a variety of substituted aromatic alkenes, giving access after Tamao oxidation to almost optically pure benzylic alcohols in high yields.
J. F. Jensen, B. Y. Svendsen, T. V. la Cour, H. L. Pedersen, M. Johannsen, J. Am. Chem. Soc., 2002, 124, 4558-4559.

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The Rh-catalyzed cross-coupling between ArZnI and TMSCH2I gave various functionalized benzylsilanes in good yields. A mechanism is proposed.
H. Takahashi, K. M. Hossain, Y. Nishihara, T. Shibata, K. Takagi, J. Org. Chem., 2006, 71, 671-675.