Patents by Inventor Robert H. Grubbs

Robert H. Grubbs has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Patent number: 11104693
    Abstract: The present disclosure is directed to methods for dehydrogenatively coupled hydrosilanes and alcohols, the methods comprising contacting an organic substrate having at least one organic alcohol moiety with a mixture of at least one hydrosilane and sodium and/or potassium hydroxide, the contacting resulting in the formation of a dehydrogenatively coupled silyl ether. The disclosure further described associated compositions and methods of using the formed products.
    Type: Grant
    Filed: April 15, 2019
    Date of Patent: August 31, 2021
    Assignee: California Institute of Technology
    Inventors: Anton Toutov, Kerry Betz, Andrew M. Romine, Robert H. Grubbs
  • Publication number: 20210236415
    Abstract: The present disclosure is directed to fatty-acid glycerol ester derivative compounds containing a targeting bisphosphonate group. The disclosure further includes pharmaceutical or biomedical compositions comprising these compounds, and methods of using these compounds and compositions forming microbubbles. The microbubbles have affinity for metal-containing, especially calcium-containing, bodies and/or biological targets. In certain embodiments, these compositions are useful for providing targeted placement of microbubbles capable of cavitation on application of high frequency energy.
    Type: Application
    Filed: October 23, 2020
    Publication date: August 5, 2021
    Inventors: Vanessa M. Marx, Robert H. Grubbs
  • Patent number: 11069921
    Abstract: Electrolyte solutions including at least one anhydrous fluoride salt and at least one non-aqueous solvent are presented. The fluoride salt includes an organic cation having a charge center (e.g., N, P, S, or O) that does not possess a carbon in the ?-position or does not possess a carbon in the ?-position having a bound hydrogen. This salt structure facilitates its ability to be made anhydrous without decomposition. Example anhydrous fluoride salts include (2,2-dimethylpropyl)trimethylammonium fluoride and bis(2,2-dimethylpropyl)dimethylammonium fluoride. Combining these fluoride salts with at least one fluorine-containing non-aqueous solvent (e.g., bis(2,2,2-trifluoroethyl)ether; (BTFE)) promotes solubility of the salt within the non-aqueous solvents. The solvent may be a mixture of at least one non-aqueous, fluorine-containing solvent and at least one other non-aqueous, fluorine or non-fluorine containing solvent (e.g., BTFE and propionitrile or dimethoxyethane).
    Type: Grant
    Filed: June 10, 2020
    Date of Patent: July 20, 2021
    Assignees: California Institute of Technology, Honda Motor Co., Ltd.
    Inventors: Simon C. Jones, Victoria K. Davis, Christopher M. Bates, Nebojsa Momcilovic, Brett M. Savoie, Michael A. Webb, Thomas F. Miller, III, Robert H. Grubbs, Christopher Brooks, Kaoru Omichi
  • Publication number: 20210218063
    Abstract: Electrolyte solutions including at least one anhydrous fluoride salt and at least one non-aqueous solvent are presented. The fluoride salt includes an organic cation having a charge center (e.g., N, P, S, or O) that does not possess a carbon in the ?-position or does not possess a carbon in the ?-position having a bound hydrogen. This salt structure facilitates its ability to be made anhydrous without decomposition. Example anhydrous fluoride salts include (2,2-dimethylpropyl)trimethylammonium fluoride and bis(2,2-dimethylpropyl)dimethylammonium fluoride. Combining these fluoride salts with at least one fluorine-containing non-aqueous solvent (e.g., bis(2,2,2-trifluoroethyl)ether; (BTFE)) promotes solubility of the salt within the non-aqueous solvents. The solvent may be a mixture of at least one non-aqueous, fluorine-containing solvent and at least one other non-aqueous, fluorine or non-fluorine containing solvent (e.g., BTFE and propionitrile or dimethoxyethane).
    Type: Application
    Filed: March 30, 2021
    Publication date: July 15, 2021
    Applicants: CALIFORNIA INSTITUTE OF TECHNOLOGY, HONDA MOTOR CO., LTD.
    Inventors: Simon C. JONES, Victoria K. DAVIS, Christopher M. BATES, Nebojsa MOMCILOVIC, Brett M. SAVOIE, Michael A. WEBB, Thomas F. MILLER, III, Robert H. GRUBBS, Christopher BROOKS, Kaoru OMICHI
  • Patent number: 11053356
    Abstract: In an aspect, a method of synthesizing a graft copolymer comprises the steps of: copolymerizing a first macromonomer and a first reactive diluent; wherein said first macromonomer comprises a first backbone precursor directly or indirectly covalently linked to a first polymer side chain group; wherein said reactive diluent is provided in the presence of the first macromonomer at an amount selected so as to result in formation said graft copolymer having a first backbone incorporating said diluent and said first macromonomer in a first polymer block characterized by a preselected first graft density or a preselected first graft distribution of said first macromonomer. In some embodiments of this aspect, said preselected first graft density is any value selected from the range of 0.05 to 0.75. In some methods, the composition and amount of said diluent is selected to provide both a first preselected first graft density and a first preselected first graft distribution.
    Type: Grant
    Filed: March 7, 2018
    Date of Patent: July 6, 2021
    Assignee: California Institute of Technology
    Inventors: Robert H Grubbs, Tzu-Pin Lin, Alice Chang, Hsiang-Yun Chen, Christopher M Bates
  • Patent number: 11053209
    Abstract: A highly efficient, Z-selective ring-closing metathesis system for the formation of macrocycles using a stereoretentive, ruthenium-based catalyst supported by a dithiolate ligand is reported. This catalyst is demonstrated to be remarkably active as observed in initiation experiments showing complete catalyst initiation at ?20° C. within 10 min. Using easily accessible diene starting materials bearing a Z-olefin moiety, macrocyclization reactions generated products with significantly higher Z-selectivity in appreciably shorter reaction times, in higher yield, and with much lower catalyst loadings than in previously reported systems. Macrocyclic lactones ranging in size from twelve-membered to seventeen-membered rings are synthesized in moderate to high yields (68-79% yield) with excellent Z-selectivity (95%-99% Z).
    Type: Grant
    Filed: April 24, 2018
    Date of Patent: July 6, 2021
    Assignee: CALIFORNIA INSTITUTE OF TECHNOLOGY
    Inventors: Tonia S. Ahmed, Robert H. Grubbs
  • Publication number: 20210198291
    Abstract: The present disclosure is directed to hydrosilyl amines and fluorosilyl amines and methods of making the same.
    Type: Application
    Filed: March 4, 2021
    Publication date: July 1, 2021
    Inventors: Anton A. Toutov, Kerry N. Betz, Andrew M. Romine, Robert H. Grubbs
  • Patent number: 11028107
    Abstract: The present invention is directed to compositions for silylating organic substrates containing C—H or O—H bonds, especially heteroaromatic substrates. The compositions are derived from the preconditioning of mixtures of hydrosilanes or organodisilanes with bases, including metal hydroxide and metal alkoxide bases. In some embodiments, the preconditioning results in the formation of reactive silicon hydride species.
    Type: Grant
    Filed: February 22, 2017
    Date of Patent: June 8, 2021
    Assignee: California Institute of Technology
    Inventors: Anton Toutov, Wenbo Liu, David P. Schuman, Brian M. Stoltz, Robert H. Grubbs
  • Patent number: 10995105
    Abstract: The present disclosure is directed at methods of forming an N—Si silyl bond, the method comprising contacting an organic substrate comprising an aromatic amine having at least one N—H bond with a mixture comprising of (a) at least one hydrosilane and (b) at least one hydroxide or alkoxide, under conditions sufficient to form the N—Si bond. The disclosure is further directed to the compositions involved in these methods and the products that result therefrom.
    Type: Grant
    Filed: August 19, 2020
    Date of Patent: May 4, 2021
    Assignee: California Institute of Technology
    Inventors: Anton A. Toutov, Kerry N. Betz, Andrew M. Romine, Robert H. Grubbs
  • Patent number: 10995049
    Abstract: The present disclosure is directed to methods of preparing prostaglandin J natural products by stereoretentive metatheses reactions and intermediates used in the synthesis of these natural products, including the use of intermediates of Formula (I-A), where R1 is defined in the specification
    Type: Grant
    Filed: July 7, 2020
    Date of Patent: May 4, 2021
    Assignee: California Institute of Technology
    Inventors: Jiaming Li, Chen Xu, Tonia S Ahmed, Robert H Grubbs, Brian M. Stoltz
  • Publication number: 20210122701
    Abstract: The present disclosure describes methods for silylating aromatic organic substrates, and associated chemical systems, said methods comprising or consisting essentially of contacting the aromatic organic substrate with a mixture of (a) at least one organosilane and (b) at least one strong base, under conditions sufficient to silylate the aromatic substrate.
    Type: Application
    Filed: January 6, 2021
    Publication date: April 29, 2021
    Inventors: Robert H. Grubbs, Alexey Federov, Anton Toutov, Kerry N. Betz
  • Patent number: 10981878
    Abstract: Backfunctionalized imidazolinium salts and methods of synthesizing the same and NHC carbene-metal complexes therefrom. For backfunctionalized imidazolinium salts of the formula: Wherein R1 is selected from the group consisting of an ester group, an amide group, and an aromatic group; R2 is selected from the group consisting of hydrogen, an ester group, an amide group, and an aromatic group; R3 and R4 are each an aliphatic group; and X is an anion; the method comprises cyclization of a halogenated acrylate with Hünig's base in a solvent.
    Type: Grant
    Filed: August 22, 2019
    Date of Patent: April 20, 2021
    Assignee: United States of America as represented by the Secretary of the Air Force
    Inventors: Rusty L. Blanski, Robert H. Grubbs
  • Patent number: 10975038
    Abstract: Backfunctionalized imidazolinium salts and methods of synthesizing the same and NHC carbene-metal complexes therefrom. For backfunctionalized imidazolinium salts of the formula: Wherein R1 is selected from the group consisting of an ester group, an amide group, and an aromatic group; R2 is selected from the group consisting of hydrogen, an ester group, an amide group, and an aromatic group; R3 and R4 are each an aliphatic group; and X is an anion; the method comprises cyclization of a halogenated acrylate with Hünig's base in a solvent.
    Type: Grant
    Filed: August 22, 2019
    Date of Patent: April 13, 2021
    Assignee: United States of America as represented by the Secretary of the Air Force
    Inventors: Rusty L. Blanski, Robert H. Grubbs
  • Patent number: 10945946
    Abstract: The present disclosure is directed to fatty-acid glycerol ester derivative compounds containing a targeting bisphosphonate group. The disclosure further include pharmaceutical or biomedical compositions comprising these compounds, and methods of using these compounds and compositions forming microbubbles. The microbubbles have affinity for metal-containing, especially calcium-containing, bodies and/or biological targets. In certain embodiments, these compositions are useful for providing targeted placement of microbubbles capable of cavitation on application of high frequency energy.
    Type: Grant
    Filed: March 26, 2020
    Date of Patent: March 16, 2021
    Assignee: California Institute of Technology
    Inventors: Vanessa M. Marx, Robert H. Grubbs
  • Publication number: 20210053043
    Abstract: This invention relates generally to metathesis catalysts and the use of such catalysts in the metathesis of olefins and olefin compounds, more particularly, in the use of such catalysts in Z and E selective olefin metathesis reactions. The invention has utility in the fields of organometallics and organic synthesis.
    Type: Application
    Filed: November 10, 2020
    Publication date: February 25, 2021
    Inventors: Adam M. JOHNS, T. Patrick MONTGOMERY, Tonia S. AHMED, Robert H. GRUBBS, Richard L. PEDERSON
  • Patent number: 10927065
    Abstract: The present disclosure describes methods for silylating aromatic organic substrates, and associated chemical systems, said methods comprising or consisting essentially of contacting the aromatic organic substrate with a mixture of (a) at least one organosilane and (b) at least one strong base, under conditions sufficient to silylate the aromatic substrate.
    Type: Grant
    Filed: February 6, 2018
    Date of Patent: February 23, 2021
    Assignee: California Institute of Technology
    Inventors: Robert H. Grubbs, Alexey Fedorov, Anton Toutov, Kerry N. Betz
  • Publication number: 20210047348
    Abstract: The present disclosure describes methods for silylating aromatic derivatives, comprising the use of hydrosilanes and potassium hydroxide.
    Type: Application
    Filed: October 20, 2020
    Publication date: February 18, 2021
    Inventors: Anton Toutov, Kerry Betz, Alexey Fedorov, Brian M. Stoltz, Wenbo Liu, Robert H. Grubbs
  • Patent number: 10919917
    Abstract: The present disclosure describes methods for silylating heteroaromatic derivatives, comprising the use of hydrosilanes and potassium hydroxide.
    Type: Grant
    Filed: December 6, 2019
    Date of Patent: February 16, 2021
    Assignee: California Institute of Technology
    Inventors: Anton Toutov, Kerry Betz, Alexey Fedorov, Brian M. Stoltz, Wenbo Liu, Robert H. Grubbs
  • Patent number: 10919860
    Abstract: Backfunctionalized imidazolinium salts and methods of synthesizing the same and NHC carbene-metal complexes therefrom. For backfunctionalized imidazolinium salts of the formula: Wherein R1 is selected from the group consisting of an ester group, an amide group, and an aromatic group; R2 is selected from the group consisting of hydrogen, an ester group, an amide group, and an aromatic group; R3 and R4 are each an aliphatic group; and X is an anion; the method comprises cyclization of a halogenated acrylate with Hünig's base in a solvent.
    Type: Grant
    Filed: August 22, 2019
    Date of Patent: February 16, 2021
    Assignee: United States of America as represented by the Secretary of the Air Force
    Inventors: Rusty L. Blanski, Robert H. Grubbs
  • Patent number: 10913723
    Abstract: Backfunctionalized imidazolinium salts and methods of synthesizing the same and NHC carbene-metal complexes therefrom. For backfunctionalized imidazolinium salts of the formula: Wherein R1 is selected from the group consisting of an ester group, an amide group, and an aromatic group; R2 is selected from the group consisting of hydrogen, an ester group, an amide group, and an aromatic group; R3 and R4 are each an aliphatic group; and X is an anion; the method comprises cyclization of a halogenated acrylate with Hünig's base in a solvent.
    Type: Grant
    Filed: August 22, 2019
    Date of Patent: February 9, 2021
    Assignee: United States of America as represented by the Secretary of the Air Force
    Inventors: Rusty L. Blanski, Robert H. Grubbs