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

Pure And Applied Chemistry

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46 Citations (Scopus)

104 Downloads (Pure)

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

ring-closing metathesis
N-heterocyclic carbenes
mechanism
Hoveyda-Grubbs type complexes
opening/cross metathesis
efficient
olefin metathesis
new generation
kinetic studies
chemical stability
cross metathesis
sterically hindered olefins
relevant

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10.1021/cs400013z

Nelson-etal-ACSC2013-Synergic-effects-between-n-heterocyclic-carbene-and-chelating-benzylideneFinal published version, 1.19 MBLicence: CC BY 4.0

Cite this

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 = "ring-closing metathesis, N-heterocyclic carbenes, mechanism, Hoveyda-Grubbs type complexes, opening/cross metathesis, efficient, olefin metathesis, new generation, kinetic studies, chemical stability, cross metathesis, sterically hindered olefins, relevant",

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",

number = "2",

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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 - ring-closing metathesis

KW - N-heterocyclic carbenes

KW - mechanism

KW - Hoveyda-Grubbs type complexes

KW - opening/cross metathesis

KW - efficient

KW - olefin metathesis

KW - new generation

KW - kinetic studies

KW - chemical stability

KW - cross metathesis

KW - sterically hindered olefins

KW - relevant

UR - http://pubs.acs.org/journal/accacs

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

Abstract

Keywords

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Quantifying the Interplay of Structure and Reactivity in Ring Closing Metathesis (QuIStRiC)

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

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

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Quantifying the Interplay of Structure and Reactivity in Ring Closing Metathesis (QuIStRiC)

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