Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 67, Issue 6, Pages 1936-1940Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo016279z
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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.
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