Searching for the hidden hydrides: The competition between alkene isomerization and metathesis with grubbs catalysts

Ian W. Ashworth; Ian H. Hillier; David J. Nelson; Jonathan M. Percy; Mark A. Vincent

doi:10.1002/ejoc.201201036

Searching for the hidden hydrides: The competition between alkene isomerization and metathesis with grubbs catalysts

Ian W. Ashworth, Ian H. Hillier, David J. Nelson, Jonathan M. Percy, Mark A. Vincent

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

Abstract

Although Grubbs metathesis catalysts have enabled syntheses of a range of molecules, alkene isomerization, a known and problematic side reaction, is poorly understood. Several mechanisms which have been advanced to account for isomerization were studied by using electronic structure calculations. The pathway catalyzed by a ruthenium hydride emerged as the most facile process by a significant margin. For the first time, we have obtained experimental evidence for the presence of this species in a metathesis-active system. © 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Original language	English
Pages (from-to)	5673-5677
Number of pages	4
Journal	European Journal of Organic Chemistry
Issue number	29
DOIs	https://doi.org/10.1002/ejoc.201201036
Publication status	Published - Oct 2012

Keywords

Density functional calculations
Homogeneous catalysis
Kinetics
Metathesis
Ruthenium

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title = "Searching for the hidden hydrides: The competition between alkene isomerization and metathesis with grubbs catalysts",

abstract = "Although Grubbs metathesis catalysts have enabled syntheses of a range of molecules, alkene isomerization, a known and problematic side reaction, is poorly understood. Several mechanisms which have been advanced to account for isomerization were studied by using electronic structure calculations. The pathway catalyzed by a ruthenium hydride emerged as the most facile process by a significant margin. For the first time, we have obtained experimental evidence for the presence of this species in a metathesis-active system. {\textcopyright} 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.",

keywords = "Density functional calculations, Homogeneous catalysis, Kinetics, Metathesis, Ruthenium",

author = "Ashworth, {Ian W.} and Hillier, {Ian H.} and Nelson, {David J.} and Percy, {Jonathan M.} and Vincent, {Mark A.}",

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AU - Ashworth, Ian W.

AU - Hillier, Ian H.

AU - Nelson, David J.

AU - Percy, Jonathan M.

AU - Vincent, Mark A.

N1 - 012MY Times Cited:0 Cited References Count:44

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N2 - Although Grubbs metathesis catalysts have enabled syntheses of a range of molecules, alkene isomerization, a known and problematic side reaction, is poorly understood. Several mechanisms which have been advanced to account for isomerization were studied by using electronic structure calculations. The pathway catalyzed by a ruthenium hydride emerged as the most facile process by a significant margin. For the first time, we have obtained experimental evidence for the presence of this species in a metathesis-active system. © 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

AB - Although Grubbs metathesis catalysts have enabled syntheses of a range of molecules, alkene isomerization, a known and problematic side reaction, is poorly understood. Several mechanisms which have been advanced to account for isomerization were studied by using electronic structure calculations. The pathway catalyzed by a ruthenium hydride emerged as the most facile process by a significant margin. For the first time, we have obtained experimental evidence for the presence of this species in a metathesis-active system. © 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

KW - Density functional calculations

KW - Homogeneous catalysis

KW - Kinetics

KW - Metathesis

KW - Ruthenium

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M3 - Article

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JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 29

ER -

Searching for the hidden hydrides: The competition between alkene isomerization and metathesis with grubbs catalysts

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Keywords

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