Highly efficient B(C6F5)3-catalyzed hydrosilylation of olefins

Michael Rubin; Todd Schwier; Vladimir Gevorgyan

doi:10.1021/jo016279z

Highly efficient B(C₆F₅)₃-catalyzed hydrosilylation of olefins

Michael Rubin, Todd Schwier, Vladimir Gevorgyan

Research output: Contribution to journal › Article › peer-review

236 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	1936-1940
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	67
Issue number	6
DOIs	https://doi.org/10.1021/jo016279z
State	Published - Mar 22 2002
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo016279z

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title = "Highly efficient B(C6F5)3-catalyzed hydrosilylation of olefins",

abstract = "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.",

author = "Michael Rubin and Todd Schwier and Vladimir Gevorgyan",

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doi = "10.1021/jo016279z",

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T1 - Highly efficient B(C6F5)3-catalyzed hydrosilylation of olefins

AU - Rubin, Michael

AU - Schwier, Todd

AU - Gevorgyan, Vladimir

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Y1 - 2002/3/22

N2 - 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.

AB - 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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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

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ER -

Highly efficient B(C₆F₅)₃-catalyzed hydrosilylation of olefins

Abstract

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