Synergic effects between N-heterocyclic carbene and chelating benzylidene-ether ligands toward the initiation step of Hoveyda-Grubbs type Ru complexes

David J. Nelson; Pierre Queval; Mathieu Rouen; Magaly Magrez; Loic Toupet; Frederic Caijo; Etienne Borre; Isabelle Laurent; Christophe Crevisy; Olivier Basle; Marc Mauduit; Jonathan M. Percy

doi:10.1021/cs400013z

Synergic effects between N-heterocyclic carbene and chelating benzylidene-ether ligands toward the initiation step of Hoveyda-Grubbs type Ru complexes

David J. Nelson, Pierre Queval, Mathieu Rouen, Magaly Magrez, Loic Toupet, Frederic Caijo, Etienne Borre, Isabelle Laurent, Christophe Crevisy, Olivier Basle, Marc Mauduit^*, Jonathan M. Percy

^*Corresponding author for this work

School of Chemistry

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

Abstract

Synergic effects between ancillary N-heterocyclic carbenes [(1,3-bis(2,4,6-trimethylphenyl)-1,3-imidazoline-2-ylidene or 1,3-bis(2,6-diisopropylphenyl)-1,3-imidazoline-2-ylidene] and chelating benzylidene ether ligands were investigated by studying initiation rates and kinetic profiles of Hoveyda-Grubbs (HG) type Ru complexes. A newly designed Ru-benzylidene-oxazinone precatalyst 4 was compared with Grela and Blechert complexes bearing modified isopropyloxy chelating leaving groups and with the standard HG complex to understand how the ancillary and the leaving ligands interact and influence the catalytic activity.

Original language	English
Pages (from-to)	259-264
Number of pages	6
Journal	ACS Catalysis
Volume	3
Issue number	2
DOIs	https://doi.org/10.1021/cs400013z
Publication status	Published - Feb 2013

Keywords

N-heterocyclic carbenes
Olefin metathesis
Kinetic studies
Hoveyda-Grubbs type complexes
Chemical stability

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10.1021/cs400013z

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Nelson, D. J., Queval, P., Rouen, M., Magrez, M., Toupet, L., Caijo, F., Borre, E., Laurent, I., Crevisy, C., Basle, O., Mauduit, M., & Percy, J. M. (2013). Synergic effects between N-heterocyclic carbene and chelating benzylidene-ether ligands toward the initiation step of Hoveyda-Grubbs type Ru complexes. ACS Catalysis, 3(2), 259-264. https://doi.org/10.1021/cs400013z

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title = "Synergic effects between N-heterocyclic carbene and chelating benzylidene-ether ligands toward the initiation step of Hoveyda-Grubbs type Ru complexes",

abstract = "Synergic effects between ancillary N-heterocyclic carbenes [(1,3-bis(2,4,6-trimethylphenyl)-1,3-imidazoline-2-ylidene or 1,3-bis(2,6-diisopropylphenyl)-1,3-imidazoline-2-ylidene] and chelating benzylidene ether ligands were investigated by studying initiation rates and kinetic profiles of Hoveyda-Grubbs (HG) type Ru complexes. A newly designed Ru-benzylidene-oxazinone precatalyst 4 was compared with Grela and Blechert complexes bearing modified isopropyloxy chelating leaving groups and with the standard HG complex to understand how the ancillary and the leaving ligands interact and influence the catalytic activity.",

keywords = "N-heterocyclic carbenes, Olefin metathesis, Kinetic studies, Hoveyda-Grubbs type complexes, Chemical stability",

author = "Nelson, \{David J.\} and Pierre Queval and Mathieu Rouen and Magaly Magrez and Loic Toupet and Frederic Caijo and Etienne Borre and Isabelle Laurent and Christophe Crevisy and Olivier Basle and Marc Mauduit and Percy, \{Jonathan M.\}",

year = "2013",

month = feb,

doi = "10.1021/cs400013z",

language = "English",

volume = "3",

pages = "259--264",

journal = "ACS Catalysis",

issn = "2155-5435",

publisher = "American Chemical Society (ACS)",

number = "2",

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TY - JOUR

T1 - Synergic effects between N-heterocyclic carbene and chelating benzylidene-ether ligands toward the initiation step of Hoveyda-Grubbs type Ru complexes

AU - Nelson, David J.

AU - Queval, Pierre

AU - Rouen, Mathieu

AU - Magrez, Magaly

AU - Toupet, Loic

AU - Caijo, Frederic

AU - Borre, Etienne

AU - Laurent, Isabelle

AU - Crevisy, Christophe

AU - Basle, Olivier

AU - Mauduit, Marc

AU - Percy, Jonathan M.

PY - 2013/2

Y1 - 2013/2

N2 - Synergic effects between ancillary N-heterocyclic carbenes [(1,3-bis(2,4,6-trimethylphenyl)-1,3-imidazoline-2-ylidene or 1,3-bis(2,6-diisopropylphenyl)-1,3-imidazoline-2-ylidene] and chelating benzylidene ether ligands were investigated by studying initiation rates and kinetic profiles of Hoveyda-Grubbs (HG) type Ru complexes. A newly designed Ru-benzylidene-oxazinone precatalyst 4 was compared with Grela and Blechert complexes bearing modified isopropyloxy chelating leaving groups and with the standard HG complex to understand how the ancillary and the leaving ligands interact and influence the catalytic activity.

AB - Synergic effects between ancillary N-heterocyclic carbenes [(1,3-bis(2,4,6-trimethylphenyl)-1,3-imidazoline-2-ylidene or 1,3-bis(2,6-diisopropylphenyl)-1,3-imidazoline-2-ylidene] and chelating benzylidene ether ligands were investigated by studying initiation rates and kinetic profiles of Hoveyda-Grubbs (HG) type Ru complexes. A newly designed Ru-benzylidene-oxazinone precatalyst 4 was compared with Grela and Blechert complexes bearing modified isopropyloxy chelating leaving groups and with the standard HG complex to understand how the ancillary and the leaving ligands interact and influence the catalytic activity.

KW - N-heterocyclic carbenes

KW - Olefin metathesis

KW - Kinetic studies

KW - Hoveyda-Grubbs type complexes

KW - Chemical stability

UR - https://www.scopus.com/pages/publications/84873349714

U2 - 10.1021/cs400013z

DO - 10.1021/cs400013z

M3 - Article

SN - 2155-5435

VL - 3

SP - 259

EP - 264

JO - ACS Catalysis

JF - ACS Catalysis

IS - 2

ER -

Synergic effects between N-heterocyclic carbene and chelating benzylidene-ether ligands toward the initiation step of Hoveyda-Grubbs type Ru complexes

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Keywords

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