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Highly Selective and Practical Hydrolytic Oxidation of Organosilanes to Silanols Catalyzed by a Ruthenium Complex

Myunghee Lee, Sangwon Ko and Sukbok Chang*

*Department of Chemistry, Ewha Womans University Seoul 120-750, Korea, Email: sbchangkaist.ac.kr

M. Lee, S. Ko, S. Chang, J. Am. Chem. Soc., 2000, 122, 12011-12012.

DOI: 10.1021/ja003079g


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Abstract

With [RuCl2(p-cymene)]2/H2O as oxidizing system, a wide range of organosilanols could be obtained with remarkably high selectivities and in excellent yields from readily available silanes. The reaction conditions are mild enough to be applicable to large-scale conversions.

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Details

The document discusses a highly selective and practical method for the hydrolytic oxidation of organosilanes to silanols using a ruthenium complex as a catalyst. Organosilanes are important in the production of silicon-based materials and in organic synthesis. Traditional methods for converting organosilanes to silanols have limitations, such as producing unwanted by-products or requiring harsh conditions. The study explores the use of various ruthenium and rhodium catalysts, with [RuCl2(p-cymene)]2 showing the highest efficiency and selectivity. This catalyst, in the presence of water, converts organosilanes to silanols with minimal formation of disiloxane by-products. The reaction is effective at room temperature and can be scaled up for larger processes. The method is also applicable to silanes with various functional groups, including alkynyl and alkenyl groups, without affecting the efficiency. Additionally, the oxidation of optically active silanes proceeds with inversion of configuration at the silicon center. The proposed mechanism involves the formation of a silylmetal hydride intermediate, which is attacked by water. This method offers a mild, efficient, and scalable approach to producing organosilanols with high selectivity and yield.


[RuCl2(p-cymene)]2 on Carbon: An Efficient, Selective, Reusable, and Environmentally Versatile Heterogeneous Catalyst

E. Choi, C. Lee, Y. Na, S. Chang, Org. Lett., 2002, 4, 2369-2371.


Key Words

silanols


ID: J48-Y2000