Highly Efficient B(C6F5)3-Catalyzed Hydrosilylation of Olefins†
journal contributionposted 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 CC 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.