Towards Long-Living Metathesis Catalysts by Tuning the N-Heterocyclic Carbene (NHC) Ligand on Trifluoroacetamide-Activated Boomerang Ru Complexes

Herve Clavier; Frederic Caijo; Etienne Borre; Diane Rix; Fabien Boeda; Steven P. Nolan; Marc Mauduit

doi:10.1002/ejoc.200900407

Towards Long-Living Metathesis Catalysts by Tuning the N-Heterocyclic Carbene (NHC) Ligand on Trifluoroacetamide-Activated Boomerang Ru Complexes

Herve Clavier, Frederic Caijo, Etienne Borre, Diane Rix, Fabien Boeda, Steven P. Nolan, Marc Mauduit

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

Abstract

The synthesis and characterization of three novel trifluoro-methylamido-conta-ming "boomerang" precatalysts bearing various N-heterocyclic carbene (NHC) ligands are reported. Comparative kinetic and stability studies show the significant effect of the NHC on the catalyst reaction profile. An investigation of the reaction scope for diverse metathesis transformations has allowed us to establish the influence of the NHC on catalyst activity, especially as a function of substrate steric bulk. The excellent stability of one of the novel precatalysts is disclosed, and allowed for its recovery at the end of catalytic reactions. Large-scale ring-closing metathesis, enyne-metathesis and cross-metathesis experiments have revealed the recoverability of the catalyst. ICP-MS analyses of the synthesized products reveal Ru contamination levels of less than 2.5 ppm. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

Original language	English
Pages (from-to)	4254-4265
Number of pages	12
Journal	European Journal of Organic Chemistry
Issue number	25
DOIs	https://doi.org/10.1002/ejoc.200900407
Publication status	Published - Sept 2009

Keywords

Boomerang catalysts
Metathesis
Carbene ligands
Heterocycles
Recycling
Ruthenium
RING-CLOSING METATHESIS
TAGGED RUTHENIUM COMPLEXES
OLEFIN CROSS-METATHESIS
TETRASUBSTITUTED OLEFINS
NUCLEOPHILIC CARBENE
ALKENE METATHESIS
GRUBBS CATALYSTS
NEW-GENERATION
IONIC LIQUIDS
BEARING

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10.1002/ejoc.200900407

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title = "Towards Long-Living Metathesis Catalysts by Tuning the N-Heterocyclic Carbene (NHC) Ligand on Trifluoroacetamide-Activated Boomerang Ru Complexes",

abstract = "The synthesis and characterization of three novel trifluoro-methylamido-conta-ming {"}boomerang{"} precatalysts bearing various N-heterocyclic carbene (NHC) ligands are reported. Comparative kinetic and stability studies show the significant effect of the NHC on the catalyst reaction profile. An investigation of the reaction scope for diverse metathesis transformations has allowed us to establish the influence of the NHC on catalyst activity, especially as a function of substrate steric bulk. The excellent stability of one of the novel precatalysts is disclosed, and allowed for its recovery at the end of catalytic reactions. Large-scale ring-closing metathesis, enyne-metathesis and cross-metathesis experiments have revealed the recoverability of the catalyst. ICP-MS analyses of the synthesized products reveal Ru contamination levels of less than 2.5 ppm. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)",

keywords = "Boomerang catalysts, Metathesis, Carbene ligands, Heterocycles, Recycling, Ruthenium, RING-CLOSING METATHESIS, TAGGED RUTHENIUM COMPLEXES, OLEFIN CROSS-METATHESIS, TETRASUBSTITUTED OLEFINS, NUCLEOPHILIC CARBENE, ALKENE METATHESIS, GRUBBS CATALYSTS, NEW-GENERATION, IONIC LIQUIDS, BEARING",

author = "Herve Clavier and Frederic Caijo and Etienne Borre and Diane Rix and Fabien Boeda and Nolan, {Steven P.} and Marc Mauduit",

year = "2009",

month = sep,

doi = "10.1002/ejoc.200900407",

language = "English",

pages = "4254--4265",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH, Weinheim",

number = "25",

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T1 - Towards Long-Living Metathesis Catalysts by Tuning the N-Heterocyclic Carbene (NHC) Ligand on Trifluoroacetamide-Activated Boomerang Ru Complexes

AU - Clavier, Herve

AU - Caijo, Frederic

AU - Borre, Etienne

AU - Rix, Diane

AU - Boeda, Fabien

AU - Nolan, Steven P.

AU - Mauduit, Marc

PY - 2009/9

Y1 - 2009/9

N2 - The synthesis and characterization of three novel trifluoro-methylamido-conta-ming "boomerang" precatalysts bearing various N-heterocyclic carbene (NHC) ligands are reported. Comparative kinetic and stability studies show the significant effect of the NHC on the catalyst reaction profile. An investigation of the reaction scope for diverse metathesis transformations has allowed us to establish the influence of the NHC on catalyst activity, especially as a function of substrate steric bulk. The excellent stability of one of the novel precatalysts is disclosed, and allowed for its recovery at the end of catalytic reactions. Large-scale ring-closing metathesis, enyne-metathesis and cross-metathesis experiments have revealed the recoverability of the catalyst. ICP-MS analyses of the synthesized products reveal Ru contamination levels of less than 2.5 ppm. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

AB - The synthesis and characterization of three novel trifluoro-methylamido-conta-ming "boomerang" precatalysts bearing various N-heterocyclic carbene (NHC) ligands are reported. Comparative kinetic and stability studies show the significant effect of the NHC on the catalyst reaction profile. An investigation of the reaction scope for diverse metathesis transformations has allowed us to establish the influence of the NHC on catalyst activity, especially as a function of substrate steric bulk. The excellent stability of one of the novel precatalysts is disclosed, and allowed for its recovery at the end of catalytic reactions. Large-scale ring-closing metathesis, enyne-metathesis and cross-metathesis experiments have revealed the recoverability of the catalyst. ICP-MS analyses of the synthesized products reveal Ru contamination levels of less than 2.5 ppm. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

KW - Boomerang catalysts

KW - Metathesis

KW - Carbene ligands

KW - Heterocycles

KW - Recycling

KW - Ruthenium

KW - RING-CLOSING METATHESIS

KW - TAGGED RUTHENIUM COMPLEXES

KW - OLEFIN CROSS-METATHESIS

KW - TETRASUBSTITUTED OLEFINS

KW - NUCLEOPHILIC CARBENE

KW - ALKENE METATHESIS

KW - GRUBBS CATALYSTS

KW - NEW-GENERATION

KW - IONIC LIQUIDS

KW - BEARING

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U2 - 10.1002/ejoc.200900407

DO - 10.1002/ejoc.200900407

M3 - Article

SN - 1434-193X

SP - 4254

EP - 4265

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 25

ER -

Towards Long-Living Metathesis Catalysts by Tuning the N-Heterocyclic Carbene (NHC) Ligand on Trifluoroacetamide-Activated Boomerang Ru Complexes

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