Ruthenium Hydride Catalyzed Silylvinylation of Internal Alkynes Using Ethylene as an Additive

Robert J. Wilson; Lauren Kaminsky; Ijaz Ahmed; Daniel A. Clark

doi:10.1021/acs.joc.5b01374

Ruthenium Hydride Catalyzed Silylvinylation of Internal Alkynes Using Ethylene as an Additive

Robert J. Wilson, Lauren Kaminsky, Ijaz Ahmed, Daniel A. Clark

Department of Chemistry

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

5 Scopus citations

Abstract

An efficient synthetic strategy for the regiospecific silylvinylation of internal alkynes is described. This transformation is catalyzed by RuHCl(CO)(SIMes)PPh₃ and provides a net 5-exo-dig trans-silylvinylation of internal alkynes. Ethylene was used to decrease reaction times and displayed altered selectivity at increased pressure. Furthermore, alkyl-substituted alkynes were acceptable substrates at 80 psi of ethylene.

Original language	English (US)
Pages (from-to)	8290-8299
Number of pages	10
Journal	Journal of Organic Chemistry
Volume	80
Issue number	16
DOIs	https://doi.org/10.1021/acs.joc.5b01374
State	Published - Aug 21 2015

ASJC Scopus subject areas

Organic Chemistry

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abstract = "An efficient synthetic strategy for the regiospecific silylvinylation of internal alkynes is described. This transformation is catalyzed by RuHCl(CO)(SIMes)PPh3 and provides a net 5-exo-dig trans-silylvinylation of internal alkynes. Ethylene was used to decrease reaction times and displayed altered selectivity at increased pressure. Furthermore, alkyl-substituted alkynes were acceptable substrates at 80 psi of ethylene.",

author = "Wilson, {Robert J.} and Lauren Kaminsky and Ijaz Ahmed and Clark, {Daniel A.}",

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language = "English (US)",

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AU - Wilson, Robert J.

AU - Kaminsky, Lauren

AU - Ahmed, Ijaz

AU - Clark, Daniel A.

PY - 2015/8/21

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N2 - An efficient synthetic strategy for the regiospecific silylvinylation of internal alkynes is described. This transformation is catalyzed by RuHCl(CO)(SIMes)PPh3 and provides a net 5-exo-dig trans-silylvinylation of internal alkynes. Ethylene was used to decrease reaction times and displayed altered selectivity at increased pressure. Furthermore, alkyl-substituted alkynes were acceptable substrates at 80 psi of ethylene.

AB - An efficient synthetic strategy for the regiospecific silylvinylation of internal alkynes is described. This transformation is catalyzed by RuHCl(CO)(SIMes)PPh3 and provides a net 5-exo-dig trans-silylvinylation of internal alkynes. Ethylene was used to decrease reaction times and displayed altered selectivity at increased pressure. Furthermore, alkyl-substituted alkynes were acceptable substrates at 80 psi of ethylene.

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Ruthenium Hydride Catalyzed Silylvinylation of Internal Alkynes Using Ethylene as an Additive

Abstract

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