Catalyst Screening by Electrospray Ionization Tandem Mass Spectrometry: Hofmann Carbenes for Olefin Metathesis

A new screening methodology, which combines in situ synthesis of complexes with an assay by electrospray ionization tandem mass spectrometry (ESI‐MS), is introduced in order to investigate highly active, cationic ruthenium–carbene catalysts in ring‐opening metathesis polymerization (ROMP). The param...

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Veröffentlicht in:Chemistry : a European journal Jg. 7; H. 21; S. 4621 - 4632
Hauptverfasser: Volland, Martin August Otfried, Adlhart, Christian, Kiener, Christoph Alexander, Chen, Peter, Hofmann, Peter
Format: Journal Article
Sprache:Englisch
Veröffentlicht: Weinheim WILEY-VCH Verlag GmbH 05.11.2001
WILEY‐VCH Verlag GmbH
Schlagworte:
carbene ligands
high-throughput screening
mass spectrometry
metathesis
ruthenium
ISSN:0947-6539, 1521-3765
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Abstract A new screening methodology, which combines in situ synthesis of complexes with an assay by electrospray ionization tandem mass spectrometry (ESI‐MS), is introduced in order to investigate highly active, cationic ruthenium–carbene catalysts in ring‐opening metathesis polymerization (ROMP). The parameter space, whic is defined by systematic variation of four structural features of the catalyst [{R2P(CH2)nPR2‐κ2P}XRu=CHR′]+ (the halogen ligand, the diphosphane bite‐angle, the steric bulk of the phosphane, and the carbene ligand) and the variation of the metathesis substrate, is mapped out. Chloride as the anionic ligand X, a small chelating angle (n=1), and reduced steric demand of the substituents R (Cy versus tBu) lead to the most reactive complex in acyclic olefin metathesis, whereas variation of the carbene moiety CHR′ has only a modest influence. The overall rate in the gas phase depends on the π‐complex preequilibrium and metallacyclobutane formation, which was found to be the rate‐determining step. In ROMP reactions backbiting has a profound influence on the overall rate. Moreover, we were able to establish that the reactivity trends determined in the gas phase parallel solution‐phase reactivity. The overall rate in solution is also determined by a favorable dimer/monomer preequilibrium providing the active catalyst by facile dissociation of dicationic, dinuclear catalyst precursors. A new and efficient high‐throughput screening methodology, which combines in situ synthesis of catalysts with an assay by electrospray ionization tandem mass spectrometry (ESI‐MS), is introduced in order to investigate the highly active olefin metathesis ruthenium–carbene catalysts [{R2P(CH2)nPR2‐κ2P}XRu=CHR′]+. A five‐dimensional parameter space was scanned in a total of 1800 experiments (see diagram). The study reveals how structural modifications and the nature of the substrate govern catalyst reactivity towards olefins and uncovers key mechanistic details.
AbstractList A new screening methodology, which combines in situ synthesis of complexes with an assay by electrospray ionization tandem mass spectrometry (ESI-MS), is introduced in order to investigate highly active, cationic ruthenium-carbene catalysts in ring-opening metathesis polymerization (ROMP). The parameter space, whic is defined by systematic variation of four structural features of the catalyst [[R2P(CH2),PR2-kappa2-P]XRu=CHR']+ (the halogen ligand, the diphosphane bite-angle, the steric bulk of the phosphane, and the carbene ligand) and the variation of the metathesis substrate, is mapped out. Chloride as the anionic ligand X, a small chelating angle (n = 1), and reduced steric demand of the substituents R (Cy versus tBu) lead to the most reactive complex in acyclic olefin metathesis, whereas variation of the carbene moiety CHR' has only a modest influence. The overall rate in the gas phase depends on the pi-complex preequilibrium and metallacyclobutane formation, which was found to be the rate-determining step. In ROMP reactions backbiting has a profound influence on the overall rate. Moreover, we were able to establish that the reactivity trends determined in the gas phase parallel solution-phase reactivity. The overall rate in solution is also determined by a favorable dimer/ monomer preequilibrium providing the active catalyst by facile dissociation of dicationic, dinuclear catalyst precursors.
A new screening methodology, which combines in situ synthesis of complexes with an assay by electrospray ionization tandem mass spectrometry (ESI-MS), is introduced in order to investigate highly active, cationic ruthenium-carbene catalysts in ring-opening metathesis polymerization (ROMP). The parameter space, whic is defined by systematic variation of four structural features of the catalyst [[R2P(CH2),PR2-kappa2-P]XRu=CHR']+ (the halogen ligand, the diphosphane bite-angle, the steric bulk of the phosphane, and the carbene ligand) and the variation of the metathesis substrate, is mapped out. Chloride as the anionic ligand X, a small chelating angle (n = 1), and reduced steric demand of the substituents R (Cy versus tBu) lead to the most reactive complex in acyclic olefin metathesis, whereas variation of the carbene moiety CHR' has only a modest influence. The overall rate in the gas phase depends on the pi-complex preequilibrium and metallacyclobutane formation, which was found to be the rate-determining step. In ROMP reactions backbiting has a profound influence on the overall rate. Moreover, we were able to establish that the reactivity trends determined in the gas phase parallel solution-phase reactivity. The overall rate in solution is also determined by a favorable dimer/ monomer preequilibrium providing the active catalyst by facile dissociation of dicationic, dinuclear catalyst precursors.A new screening methodology, which combines in situ synthesis of complexes with an assay by electrospray ionization tandem mass spectrometry (ESI-MS), is introduced in order to investigate highly active, cationic ruthenium-carbene catalysts in ring-opening metathesis polymerization (ROMP). The parameter space, whic is defined by systematic variation of four structural features of the catalyst [[R2P(CH2),PR2-kappa2-P]XRu=CHR']+ (the halogen ligand, the diphosphane bite-angle, the steric bulk of the phosphane, and the carbene ligand) and the variation of the metathesis substrate, is mapped out. Chloride as the anionic ligand X, a small chelating angle (n = 1), and reduced steric demand of the substituents R (Cy versus tBu) lead to the most reactive complex in acyclic olefin metathesis, whereas variation of the carbene moiety CHR' has only a modest influence. The overall rate in the gas phase depends on the pi-complex preequilibrium and metallacyclobutane formation, which was found to be the rate-determining step. In ROMP reactions backbiting has a profound influence on the overall rate. Moreover, we were able to establish that the reactivity trends determined in the gas phase parallel solution-phase reactivity. The overall rate in solution is also determined by a favorable dimer/ monomer preequilibrium providing the active catalyst by facile dissociation of dicationic, dinuclear catalyst precursors.
A new screening methodology, which combines in situ synthesis of complexes with an assay by electrospray ionization tandem mass spectrometry (ESI‐MS), is introduced in order to investigate highly active, cationic ruthenium–carbene catalysts in ring‐opening metathesis polymerization (ROMP). The parameter space, whic is defined by systematic variation of four structural features of the catalyst [{R2P(CH2)nPR2‐κ2P}XRu=CHR′]+ (the halogen ligand, the diphosphane bite‐angle, the steric bulk of the phosphane, and the carbene ligand) and the variation of the metathesis substrate, is mapped out. Chloride as the anionic ligand X, a small chelating angle (n=1), and reduced steric demand of the substituents R (Cy versus tBu) lead to the most reactive complex in acyclic olefin metathesis, whereas variation of the carbene moiety CHR′ has only a modest influence. The overall rate in the gas phase depends on the π‐complex preequilibrium and metallacyclobutane formation, which was found to be the rate‐determining step. In ROMP reactions backbiting has a profound influence on the overall rate. Moreover, we were able to establish that the reactivity trends determined in the gas phase parallel solution‐phase reactivity. The overall rate in solution is also determined by a favorable dimer/monomer preequilibrium providing the active catalyst by facile dissociation of dicationic, dinuclear catalyst precursors. A new and efficient high‐throughput screening methodology, which combines in situ synthesis of catalysts with an assay by electrospray ionization tandem mass spectrometry (ESI‐MS), is introduced in order to investigate the highly active olefin metathesis ruthenium–carbene catalysts [{R2P(CH2)nPR2‐κ2P}XRu=CHR′]+. A five‐dimensional parameter space was scanned in a total of 1800 experiments (see diagram). The study reveals how structural modifications and the nature of the substrate govern catalyst reactivity towards olefins and uncovers key mechanistic details.
Author Adlhart, Christian
Kiener, Christoph Alexander
Chen, Peter
Hofmann, Peter
Volland, Martin August Otfried
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  givenname: Martin August Otfried
  surname: Volland
  fullname: Volland, Martin August Otfried
  organization: Universität Heidelberg, Organisch−Chemisches Institut Im Neuenheimer Feld 270, 69120 Heidelberg (Germany) Fax: (+49) 6221-54-4885
– sequence: 2
  givenname: Christian
  surname: Adlhart
  fullname: Adlhart, Christian
  organization: Eidgenössische Technische Hochschule Laboratorium für Organische Chemie ETH Hönggerberg, 8093 Zürich (Switzerland) Fax: (+41) 1-63-21280
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  givenname: Christoph Alexander
  surname: Kiener
  fullname: Kiener, Christoph Alexander
  organization: Universität Heidelberg, Organisch−Chemisches Institut Im Neuenheimer Feld 270, 69120 Heidelberg (Germany) Fax: (+49) 6221-54-4885
– sequence: 4
  givenname: Peter
  surname: Chen
  fullname: Chen, Peter
  email: chen@org.chem.ethz.ch
  organization: Eidgenössische Technische Hochschule Laboratorium für Organische Chemie ETH Hönggerberg, 8093 Zürich (Switzerland) Fax: (+41) 1-63-21280
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  givenname: Peter
  surname: Hofmann
  fullname: Hofmann, Peter
  email: ph@phindigo.oci.uni-heidelberg.de
  organization: Universität Heidelberg, Organisch−Chemisches Institut Im Neuenheimer Feld 270, 69120 Heidelberg (Germany) Fax: (+49) 6221-54-4885
BackLink https://www.ncbi.nlm.nih.gov/pubmed/11757654$$D View this record in MEDLINE/PubMed
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1993; 48
2001; 123
1997; 119
1996 1996 1998 1998; 108 35 110 37
1999 1999; 111 38
1993 1998; 26 54
1997 1997; 109 36
1995; 117
1998
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1998 1998 1999 1998; 110 37 111 38
1992 1992; 117
1999; 40
1992
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1999; 5
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2001; 7
2001; 617/618
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1992; 114
1997; 167
2000; 83
1997; 16
1998 1998; 108 37
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1998; 2
2001 2000 2000 1998 1998 1998; 7 112 39 280 110 37
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1981
1998 1998; 110 37
2001; 34
2000 2000; 112 39
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Snippet A new screening methodology, which combines in situ synthesis of complexes with an assay by electrospray ionization tandem mass spectrometry (ESI‐MS), is...
A new screening methodology, which combines in situ synthesis of complexes with an assay by electrospray ionization tandem mass spectrometry (ESI-MS), is...
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SubjectTerms carbene ligands
high-throughput screening
mass spectrometry
metathesis
ruthenium
Title Catalyst Screening by Electrospray Ionization Tandem Mass Spectrometry: Hofmann Carbenes for Olefin Metathesis
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