Patents by Inventor CHERN-HOOI LIM

CHERN-HOOI LIM 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).

  • Publication number: 20230406826
    Abstract: The present invention relates to a process for coupling a heterocyclic aromatic ring AR1 and a carbocyclic or heterocyclic aromatic ring AR2 to each other by a light-assisted decarboxylative carbon-carbon cross-coupling reaction, wherein a reaction medium is provided by mixing a first reactant, a second reactant and a catalyst composition, wherein the catalyst composition comprises (i) a palladium compound which is a palladium salt or a palladium complex or a mixture thereof, and (ii) a polycyclic compound of Formula (I), (II) or (III): the reaction medium is irradiated by an external light source, thereby coupling the heterocyclic aromatic ring AR1 of the first reactant to the aromatic ring AR2 of the second reactant by a decarboxylative carbon-carbon cross-coupling reaction.
    Type: Application
    Filed: April 25, 2023
    Publication date: December 21, 2023
    Inventors: Chern-Hooi LIM, Gang QIAN, William Zachary ELDER, Paige RILEY, Robin KOLVENBACH, Philipp WALTER, Michael GOCK
  • Publication number: 20230405565
    Abstract: The present invention relates to a catalyst composition for synthesis of heteroaromatic biaryls by a light-assisted decarboxylative carbon-carbon cross-coupling reaction, wherein the composition comprises (i) a palladium compound which is selected from a palladium salt or a palladium complex or a mixture thereof, (ii) at least one of the following compounds: a compound of Formula (I) a compound of Formula (II) an iridium complex comprising ligands L1, L2 and L3, wherein the ligands L1, L2 and L3 are selected, independently from each other, from a phenylpyridine and a bipyridine.
    Type: Application
    Filed: April 25, 2023
    Publication date: December 21, 2023
    Inventors: Chern-Hooi LIM, Gang QIAN, William Zachary ELDER, Paige RILEY, Robin KOLVENBACH, Philipp WALTER, Michael GOCK
  • Publication number: 20230090784
    Abstract: The disclosure relates to benzo[ghi]perylene imide photoredox catalysts (PC) and methods for the Birch reductions of aromatic substrates, such as benzene, benzeneoid, and heteroaromatic compounds, using light as the driving force. Certain aspects of the disclosure encompass methods for reduction of aromatic substrates. The method comprises contacting an aromatic substrate with a sacrificial electron donor in the presence of a photoredox catalyst in a solvent, thereby forming a reaction mixture; exposing the reaction mixture to visible or UV light under reaction condition sufficient to reduce the aromatic substrate compound.
    Type: Application
    Filed: January 11, 2021
    Publication date: March 23, 2023
    Inventors: Garret M. Miyake, Justin P. Cole, Ryan M. Pearson, Chern-Hooi Lim, Max Kudisch, Dian-Feng Chen
  • Publication number: 20230064451
    Abstract: The present invention relates to a composition, comprising a palladium compound which is a palladium salt or a palladium complex or a mixture thereof, and a polycyclic compound of Formula (I), (II) or (III):
    Type: Application
    Filed: June 15, 2022
    Publication date: March 2, 2023
    Inventors: Philipp WALTER, Robin KOLVENBACH, Michael GOCK, William Zachary ELDER, Celia Federico, David J. Boston, Harit Vora, Brent Cutcliffe, Chern-Hooi Lim
  • Patent number: 11427536
    Abstract: In one aspect, the invention provides a method of promoting a carbon-sulfur bond forming reaction. In certain embodiments, the reaction comprises cross-coupling of a(n) (hetero)aryl halide with a thiol to form the carbon-sulfur bond, wherein the method is promoted by light irradiation in the absence of a photocatalyst. In other embodiments, the cross-coupling reaction can be promoted through visible light irradiation, including sunlight.
    Type: Grant
    Filed: June 27, 2018
    Date of Patent: August 30, 2022
    Assignee: THE REGENTS OF THE UNIVERSITY OF COLORADO, A BODY CORPORATE
    Inventors: Garret Miyake, Bin Liu, Chern-Hooi Lim
  • Publication number: 20220169607
    Abstract: The present invention provides photocatalysts, methods for their preparation, and methods for preparing linear polymers with high propagation rate.
    Type: Application
    Filed: March 30, 2020
    Publication date: June 2, 2022
    Applicant: Colorado State University Research Foundation
    Inventors: Bonnie L. Buss, Garret Miyake, Chern-Hooi Lim, Max Kudisch
  • Patent number: 11345771
    Abstract: The invention provides novel compounds and methods that are useful in promoting reactions that proceed through an oxidative quenching pathway. In certain embodiments, the reactions comprise atom transfer radical polymerization.
    Type: Grant
    Filed: March 2, 2021
    Date of Patent: May 31, 2022
    Assignees: The Regents of the University of Colorado, Colorado State University Research Foundation
    Inventors: Garret Miyake, Jordan Corinne Theriot, Matthew D. Ryan, Ryan Michael Pearson, Tracy Allen French, Haishen Yang, Andrew Lockwood, Charles Musgrave, Chern-Hooi Lim, Ya Du, Blaine McCarthy
  • Publication number: 20210269558
    Abstract: The invention provides novel compounds and methods that are useful in promoting reactions that proceed through an oxidative quenching pathway. In certain embodiments, the reactions comprise atom transfer radical polymerization.
    Type: Application
    Filed: March 2, 2021
    Publication date: September 2, 2021
    Inventors: GARRET MIYAKE, JORDAN CORINNE THERIOT, MATTHEW D. RYAN, RYAN MICHAEL PEARSON, TRACY ALLEN FRENCH, HAISHEN YANG, ANDREW LOCKWOOD, CHARLES MUSGRAVE, CHERN-HOOI LIM, YA DU, BLAINE MCCARTHY
  • Patent number: 11104653
    Abstract: The disclosure relates to a method for forming aryl carbon-nitrogen bonds and to photoreactors useful in these and other light-driven reactions. The method comprises contacting an aryl halide, such as 4-bromobenzotrifluoride, with an amine, such as morpholine, in the presence of a Ni salt catalyst solution and an optional base, thereby forming a reaction mixture; exposing the reaction mixture to light under reaction condition sufficient to produce the aryl carbon-nitrogen bonds, e.g., to give a product such as 4-(4-(trifluoromethyl)phenyl)morpholine. In certain embodiments, the amine may be present in a molar excess to the aryl halide. In certain embodiments, the Ni salt catalyst solution includes a Ni(II) salt and a polar solvent, wherein the Ni(II) salt is dissolved in the polar solvent. In certain embodiments, the reactions conditions include holding the reaction mixture at between about room temperature and about 80° C.
    Type: Grant
    Filed: May 6, 2019
    Date of Patent: August 31, 2021
    Assignee: Colorado State University Research Foundation
    Inventors: Garret Miyake, Chern-Hooi Lim, Max Kudisch, Bin Liu
  • Patent number: 10975171
    Abstract: The invention provides novel compounds and methods that are useful in promoting reactions that proceed through an oxidative quenching pathway. In certain embodiments, the reactions comprise atom transfer radical polymerization.
    Type: Grant
    Filed: April 23, 2018
    Date of Patent: April 13, 2021
    Assignees: The Regents of the University of Colorado, a body corporate, Colorado State University Research Foundation
    Inventors: Garret Miyake, Jordan Corinne Theriot, Matthew D. Ryan, Ryan Michael Pearson, Tracy Allen French, Haishen Yang, Andrew Lockwood, Charles Musgrave, Chern-Hooi Lim, Ya Du, Blaine McCarthy
  • Publication number: 20200147581
    Abstract: The disclosure relates to a dual catalytic method for forming aryl carbon-nitrogen bonds. The method comprises contacting an aryl halide with an amine in the presence of a dual catalytic solution comprising a Ni(II) salt catalyst, a photocatalyst, and an optional base, thereby forming a reaction mixture; exposing the reaction mixture to light under reaction condition sufficient to produce the aryl carbon-nitrogen bonds. In certain embodiments, the amine may be present in a molar excess to the aryl halide. In certain embodiment, the photocatalyst may be [Ru(bpy)3]Cl2 or an organic phenoxazine. In certain embodiments, the Ni salt catalyst solution includes a Ni(II) salt and a polar solvent, wherein the Ni(II) salt is dissolved in the polar solvent.
    Type: Application
    Filed: November 12, 2019
    Publication date: May 14, 2020
    Applicant: COLORADO STATE UNIVERSITY RESEARCH FOUNDATION
    Inventors: Garret Miyake, Chern-Hooi Lim, Max Kudisch, Bin Liu
  • Publication number: 20190345122
    Abstract: The disclosure relates to a method for forming aryl carbon-nitrogen bonds and to photoreactors useful in these and other light-driven reactions. The method comprises contacting an aryl halide with an amine in the presence of a Ni salt catalyst solution and an optional base, thereby forming a reaction mixture; exposing the reaction mixture to light under reaction condition sufficient to produce the aryl carbon-nitrogen bonds. In certain embodiments, the amine may be present in a molar excess to the aryl halide. In certain embodiments, the Ni salt catalyst solution includes a Ni(II) salt and a polar solvent, wherein the Ni(II) salt is dissolved in the polar solvent. In certain embodiments, the reactions conditions include holding the reaction mixture at between about room temperature and about 80° C. for between about 1 hour and about 20 hours such that at least about 50% yield is obtained.
    Type: Application
    Filed: May 6, 2019
    Publication date: November 14, 2019
    Applicant: Colorado State University Research Foundation
    Inventors: Garret Miyake, Chern-Hooi Lim, Max Kudisch, Bin Liu
  • Publication number: 20180370911
    Abstract: In one aspect, the invention provides a method of promoting a carbon-sulfur bond forming reaction. In certain embodiments, the reaction comprises cross-coupling of a(n) (hetero)aryl halide with a thiol to form the carbon-sulfur bond, wherein the method is promoted by light irradiation in the absence of a photocatalyst. In other embodiments, the cross-coupling reaction can be promoted through visible light irradiation, including sunlight.
    Type: Application
    Filed: June 27, 2018
    Publication date: December 27, 2018
    Inventors: GARRET MIYAKE, BIN LIU, CHERN-HOOI LIM
  • Publication number: 20180237550
    Abstract: The invention provides novel compounds and methods that are useful in promoting reactions that proceed through an oxidative quenching pathway. In certain embodiments, the reactions comprise atom transfer radical polymerization.
    Type: Application
    Filed: April 23, 2018
    Publication date: August 23, 2018
    Inventors: GARRET MIYAKE, JORDAN CORINNE THERIOT, MATTHEW D. RYAN, RYAN MICHAEL PEARSON, TRACY ALLEN FRENCH, HAISHEN YANG, ANDREW LOCKWOOD, CHARLES MUSGRAVE, CHERN-HOOI LIM, YA DU, BLAINE MCCARTHY