Backbone tuning in indenylidene-ruthenium complexes bearing an unsaturated N-heterocyclic carbene

Cesar A. Urbina-Blanco; Xavier Bantreil; Herve Clavier; Alexandra M. Z. Slawin; Steven P. Nolan

doi:10.3762/bjoc.6.128

Backbone tuning in indenylidene-ruthenium complexes bearing an unsaturated N-heterocyclic carbene

Cesar A. Urbina-Blanco, Xavier Bantreil, Herve Clavier, Alexandra M. Z. Slawin, Steven P. Nolan

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

Abstract

The steric and electronic influence of backbone substitution in IMes-based (IMes = 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene) N-heterocyclic carbenes (NHC) was probed by synthesizing the [RhCl(CO)(2)(NHC)] series of complexes to quantify experimentally the Tolman electronic parameter (electronic) and the percent buried volume (%V-bur, steric) parameters. The corresponding ruthenium-indenylidene complexes were also synthesized and tested in benchmark metathesis transformations to establish possible correlations between reactivity and NHC electronic and steric parameters.

Original language	English
Pages (from-to)	1120-1126
Number of pages	7
Journal	Beilstein Journal of Organic Chemistry
Volume	6
DOIs	https://doi.org/10.3762/bjoc.6.128
Publication status	Published - Nov 2010

Keywords

N-heterocyclic carbene
Olefin metathesis
Percent buried volume
Ruthenium-indenylidene
Tolman electronic parameter

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10.3762/bjoc.6.128

1860-5397-6-128
© 2010 Urbina-Blanco et al; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (http://www.beilstein-journals.org/bjoc)
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EPSRC - EP/J011053/1- LATE TRANSITION: Late Transition Metal Hydroxide in Homogeneous Catalysis
Nolan, S. P. (PI)
EPSRC
15/03/12 → 14/03/15
Project: Standard

Cite this

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title = "Backbone tuning in indenylidene-ruthenium complexes bearing an unsaturated N-heterocyclic carbene",

abstract = "The steric and electronic influence of backbone substitution in IMes-based (IMes = 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene) N-heterocyclic carbenes (NHC) was probed by synthesizing the [RhCl(CO)(2)(NHC)] series of complexes to quantify experimentally the Tolman electronic parameter (electronic) and the percent buried volume (%V-bur, steric) parameters. The corresponding ruthenium-indenylidene complexes were also synthesized and tested in benchmark metathesis transformations to establish possible correlations between reactivity and NHC electronic and steric parameters.",

keywords = "N-heterocyclic carbene, Olefin metathesis, Percent buried volume, Ruthenium-indenylidene, Tolman electronic parameter",

author = "Urbina-Blanco, {Cesar A.} and Xavier Bantreil and Herve Clavier and Slawin, {Alexandra M. Z.} and Nolan, {Steven P.}",

year = "2010",

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language = "English",

volume = "6",

pages = "1120--1126",

journal = "Beilstein Journal of Organic Chemistry",

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T1 - Backbone tuning in indenylidene-ruthenium complexes bearing an unsaturated N-heterocyclic carbene

AU - Urbina-Blanco, Cesar A.

AU - Bantreil, Xavier

AU - Clavier, Herve

AU - Slawin, Alexandra M. Z.

AU - Nolan, Steven P.

PY - 2010/11

Y1 - 2010/11

N2 - The steric and electronic influence of backbone substitution in IMes-based (IMes = 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene) N-heterocyclic carbenes (NHC) was probed by synthesizing the [RhCl(CO)(2)(NHC)] series of complexes to quantify experimentally the Tolman electronic parameter (electronic) and the percent buried volume (%V-bur, steric) parameters. The corresponding ruthenium-indenylidene complexes were also synthesized and tested in benchmark metathesis transformations to establish possible correlations between reactivity and NHC electronic and steric parameters.

AB - The steric and electronic influence of backbone substitution in IMes-based (IMes = 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene) N-heterocyclic carbenes (NHC) was probed by synthesizing the [RhCl(CO)(2)(NHC)] series of complexes to quantify experimentally the Tolman electronic parameter (electronic) and the percent buried volume (%V-bur, steric) parameters. The corresponding ruthenium-indenylidene complexes were also synthesized and tested in benchmark metathesis transformations to establish possible correlations between reactivity and NHC electronic and steric parameters.

KW - N-heterocyclic carbene

KW - Olefin metathesis

KW - Percent buried volume

KW - Ruthenium-indenylidene

KW - Tolman electronic parameter

U2 - 10.3762/bjoc.6.128

DO - 10.3762/bjoc.6.128

M3 - Article

VL - 6

SP - 1120

EP - 1126

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

Backbone tuning in indenylidene-ruthenium complexes bearing an unsaturated N-heterocyclic carbene

Abstract

Keywords

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Projects

EPSRC - EP/J011053/1- LATE TRANSITION: Late Transition Metal Hydroxide in Homogeneous Catalysis

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