“Olefin Metathesis” R. H. Grubbs, Tetrahedron, 2004 , 60 , 7117-7140.
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“Olefin Metathesis” R. H. Grubbs, Tetrahedron, 2004, 60, 7117-7140. Fundamental mechanistic studies have resulted in a family of ruthenium based catalysts have been developed for the metathesis of olefins. The results of this NSF supported research are now being transitioned into applications in pharmaceuticals, fine chemicals and materials. Cy 3 P Ru PCy 3 Cl Cl Ph RCM ROMP N N Ru PCy 3 Cl Cl Ph n ADMET M etathesis Transform ations Metal Catalyzed Reactions of Hydrocarbons Robert H. Grubbs, Caltech Award #CHE-0410425, equally co-funded with DMR/POL
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Metal Catalyzed Reactions of Hydrocarbons Robert H. Grubbs, Caltech Award #CHE-0410425, equally co-funded with DMR/POL. - PowerPoint PPT Presentation
Transcript of “Olefin Metathesis” R. H. Grubbs, Tetrahedron, 2004 , 60 , 7117-7140.
“Olefin Metathesis” R. H. Grubbs, Tetrahedron, 2004, 60, 7117-7140.
Fundamental mechanistic studies have resulted in a family of ruthenium based catalysts have been developed for the metathesis of olefins. The results of this NSF supported research are now being transitioned into applications in pharmaceuticals, fine chemicals and materials.
Cy3P
Ru
PCy3
Cl
Cl
Ph
RCM
ROMP
N N
Ru
PCy3
Cl
Cl
Ph
n
ADMET
Metathesis Transformations
Metal Catalyzed Reactions of Hydrocarbons
Robert H. Grubbs, Caltech
Award #CHE-0410425, equally co-funded with DMR/POL
“Olefin Metathesis” R. H. Grubbs, Tetrahedron, 2004, 60, 7117-7140.
Fundamental mechanistic studies have resulted in a family of ruthenium based catalysts have been developed for the metathesis of olefins. A DOE/Cargill/Caltech/Materia,Inc. research agreement has just been initiated for the use of these catalysts for the conversion of the renewable resource, Seed Oils, into products normally produced from petroleum based materials. A new material will be introduced in the next few months as a commodity product.
OCO
(CH2)nCH=CH(CH2)mCH3
OCO
OCO
(CH2)oCH=CH(CH2)pCH3
(CH2)qCH=CH(CH2)rCH3
CH3(CH2)sCH=CH(CH2)tCO2CH3
Mix or pure fatty acid ester
CH3(CH2)sCH=CH(CH2)sCH3
CH3O2C(CH2)sCH=CH(CH2)tCO2CH3
+
Cross linked Oils and Waxes
Ruthenium Metathesis Catalyst
Ruthenium Metathesis Catalyst
Replacements forPetroleum basedProducts
RenewableSeed Oils
Metal Catalyzed Reactions of Hydrocarbons
Robert H. Grubbs, Caltech
Award #CHE-0410425, equally co-funded with DMR/POL
Fundamental mechanistic studies have resulted in a family of ruthenium based catalysts have been developed for the metathesis of olefins. These catalysts can be used in the preparation of a variety of polymers, materials and small molecules. The chemistry is now being used to produce a number of pharmaceuticals by ring closing metathesis that are now in phase II trials.
.
N
O
NS
N
MeO
HN
OH
O
ONH
O
O
O
NH
HCV Serine Protease Inhibitor
Boehringer Ingelheim’s BILN 2061
Hepatitus C Therapeutic
GlaxoSmithKline Osteoporosis Therapeutic
“Olefin Metathesis” R. H. Grubbs, Tetrahedron, 2004, 60, 7117-7140
NSO2Pyr
OH
N
O
O
Metal Catalyzed Reactions of Hydrocarbons
Robert H. Grubbs, Caltech
Award #CHE-0410425, equally co-funded with DMR/POL
Metal Catalyzed Reactions of Hydrocarbons
Robert H. Grubbs, Caltech
Award #CHE-0410425, equally co-funded with DMR/POL
Picture or graphic
Materia, Inc and Easton Sports
Fundamental mechanistic studies have resulted in a family of ruthenium based catalysts have been developed for the metathesis of olefins. These catalysts can be used in the preparation of a variety of polymers, materials and small molecules. On example of the application in materials is a composite wood-ROMP polymer bat that is now commercialized by Easton Sports. This application demonstrates the environmental tolerance and robustness of the chemistry.
