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Highly Efficient B(C6F5)3-Catalyzed Hydrosilylation of Olefins

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journal contribution
posted on 26.02.2002, 00:00 by Michael Rubin, Todd Schwier, Vladimir Gevorgyan
A convenient and highly efficient method for the Lewis acid-catalyzed trans-selective hydrosilylation of alkenes has been developed. The mechanism of this novel protocol operates via direct addition of silylium type species across CC bond followed by trapping of the resultant carbenium ion with boron-bound hydride. A number of diversely substituted silanes possessing both aryl and alkyl groups at silicon atom were efficiently prepared using this hydrosilylation methodology. The possibility to employ aryl-containing hydrosilanes in this reaction opens broad capabilities for the synthesis of alcohols via a trans-selective hydrosilylation/Tamao−Fleming oxidation sequence, complementary to the existing cis-selective hydroboration/oxidation protocol.