Patents by Inventor Xumu Zhang

Xumu Zhang 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: 20220185835
    Abstract: The present invention relates to the technical field of chiral synthesis, and specifically provides the synthesis and use of a new type of oxa-spirodiphosphine ligands. The bisphosphine ligand is prepared with oxa-spirobisphenol as a starting material after triflation, palladium catalyzed coupling with diaryl phosphine oxide, reduction of trichlorosilane, further palladium catalyzed coupling with diaryl phosphine oxide, and further reduction of trichlorosilane. The oxa-spiro compound has central chirality, and thus includes L-oxa-spirodiphosphine ligand and R-oxa-spirodiphosphine ligand. The racemic spirodiphosphine ligand is capable of being synthesized from racemic oxa-spirobisphenol as a raw material. The present invention can be used as a chiral ligand in the asymmetric hydrogenation of unsaturated carboxylic acids. The complex of the ligand with ruthenium can achieve an enantioselectivity of greater than 99% in the asymmetric hydrogenation of methyl-cinnamic acid.
    Type: Application
    Filed: March 8, 2022
    Publication date: June 16, 2022
    Inventors: XUMU ZHANG, GENQIANG CHEN, JIAMING HUANG
  • Patent number: 11299507
    Abstract: The present invention relates to the technical field of chiral synthesis, and specifically provides a new type of oxa-spirodiphosphine ligands. The bisphosphine ligand is prepared with oxa-spirobisphenol as a starting material after triflation, palladium catalyzed coupling with diaryl phosphine oxide, reduction of trichlorosilane, further palladium catalyzed coupling with diaryl phosphine oxide, and further reduction of trichlorosilane. The oxa-spiro compound has central chirality, and thus includes L-oxa-spirodiphosphine ligand and R-oxa-spirodiphosphine ligand. The racemic spirodiphosphine ligand is capable of being synthesized from racemic oxa-spirobisphenol as a raw material. The present invention can be used as a chiral ligand in the asymmetric hydrogenation of unsaturated carboxylic acids. The complex of the ligand with ruthenium can achieve an enantioselectivity of greater than 99% in the asymmetric hydrogenation of methyl-cinnamic acid.
    Type: Grant
    Filed: February 8, 2018
    Date of Patent: April 12, 2022
    Assignee: SHENZHEN CATALYS TECHNOLOGY CO., LTD.
    Inventors: Xumu Zhang, Genqiang Chen, Jiaming Huang
  • Publication number: 20210340168
    Abstract: The present invention provides an oxa-spirodiphosphine ligand having a structure of general Formula (I) below: wherein in general Formula (I), R1, R2, R3 and R4 are the same, and are alkyl, alkoxy, aryl, aryloxy, or hydrogen, in which R1, R2, R3 and R4 may or may not form a ring, any two of them may form a ring, or a polycyclic ring may be formed between two pairs of them; R5 and R6 is alkyl, aryl, or hydrogen; and R7 and R8 is alkyl, benzyl, or aryl. The present invention also provides a method for asymmetric hydrogenation of ?,?-unsaturated carboxylic acids. A complex of the oxa-spirodiphosphine ligand with ruthenium shows excellent activity and enantioselectivity in the asymmetric hydrogenation of various ?,?-unsaturated carboxylic acids, with which a chiral carboxylic acid product can be obtained with an enantioselectivity up to 99%.
    Type: Application
    Filed: April 30, 2020
    Publication date: November 4, 2021
    Inventors: Genqiang CHEN, Jiaming HUANG, Yongpeng ZHENG, Baode MA, Xumu ZHANG
  • Publication number: 20200308206
    Abstract: The present invention relates to the technical field of chiral synthesis, and specifically provides a new type of oxa-spirodiphosphine ligands. The bisphosphine ligand is prepared with oxa-spirobisphenol as a starting material after triflation, palladium catalyzed coupling with diaryl phosphine oxide, reduction of trichlorosilane, further palladium catalyzed coupling with diaryl phosphine oxide, and further reduction of trichlorosilane. The oxa-spiro compound has central chirality, and thus includes L-oxa-spirodiphosphine ligand and R-oxa-spirodiphosphine ligand. The racemic spirodiphosphine ligand is capable of being synthesized from racemic oxa-spirobisphenol as a raw material. The present invention can be used as a chiral ligand in the asymmetric hydrogenation of unsaturated carboxylic adds. The complex of the ligand with ruthenium can achieve an enantioselectivity of greater than 99% in the asymmetric hydrogenation of methyl-cinnamic acid.
    Type: Application
    Filed: February 8, 2018
    Publication date: October 1, 2020
    Inventors: Xumu ZHANG, Genqiang CHEN, Jiaming HUANG
  • Patent number: 10766833
    Abstract: A homogeneous catalytic reaction method and a catalyst for isomerization and hydroformylation of long-chain internal olefins are disclosed. A rhodium-ruthenium metal complex is used as a catalyst; and the ligands are tetradentate phosphine ligands. By means of the catalytic system, homogeneous internal olefin isomerization aid hydroformylation can be performed under a certain temperature and pressure to obtain aldehyde products having high normal to iso ratios. The present invention is applicable to not only long-chain internal olefins (?C8) but also internal olefins having a carbon number less than 8.
    Type: Grant
    Filed: July 12, 2019
    Date of Patent: September 8, 2020
    Assignee: Wuhan Catalys Technology CO., LTD
    Inventor: Xumu Zhang
  • Publication number: 20190337866
    Abstract: A homogeneous catalytic reaction method and a catalyst for isomerization and hydroformylation of long-chain internal olefins are disclosed. A rhodium-ruthenium metal complex is used as a catalyst; and the ligands are tetradentate phosphine ligands. By means of the catalytic system, homogeneous internal olefin isomerization aid hydroformylation can be performed under a certain temperature and pressure to obtain aldehyde products having high normal to iso ratios. The present invention is applicable to not only long-chain internal olefins (?C8) but also internal olefins having a carbon number less than 8.
    Type: Application
    Filed: July 12, 2019
    Publication date: November 7, 2019
    Inventor: XUMU ZHANG
  • Patent number: 9744528
    Abstract: A ligand having the structure or its enantiomer; (I) wherein: each one of Ra, Rb, Rc and Rd is selected from alkyl, cycloalkyl, and aryl; the bridge group is selected from CH2NH; *CH(CH3)NH(C*,R); and the organocatalyst is an organic molecule catalyst covalently bound to the bridge group. Also, a catalyst having the structure or its enantiomer: (II) wherein: each one of Ra, Rb, Rc and Rd is selected from alkyl, cycloalkyl, and aryl; the bridge group is selected from CH2NH; *CH(CH3)NH(C*,R); and *CH(CH3)NH(C*,S); the organocatalyst is an organic molecule catalyst covalently bound to the bridge group; and M is selected from the group consisting of Rh, Pd, Cu, Ru, Ir, Ag, Au, Zn, Ni, Co, and Fe.
    Type: Grant
    Filed: March 11, 2014
    Date of Patent: August 29, 2017
    Assignee: RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY
    Inventor: Xumu Zhang
  • Publication number: 20160023198
    Abstract: A ligand having the structure or its enantiomer; (I) wherein: each one of Ra, Rb, Rc and Rd is selected from alkyl, cycloalkyl, and aryl; the bridge group is selected from CH2NH; *CH(CH3)NH(C*,R); and the organocatalyst is an organic molecule catalyst covalently bound to the bridge group. Also, a catalyst having the structure or its enantiomer: (II) wherein: each one of Ra, Rb, Rc and Rd is selected from alkyl, cycloalkyl, and aryl; the bridge group is selected from CH2NH; *CH(CH3)NH(C*,R); and *CH(CH3)NH(C*,S); the organocatalyst is an organic molecule catalyst covalently bound to the bridge group; and M is selected from the group consisting of Rh, Pd, Cu, Ru, Ir, Ag, Au, Zn, Ni, Co, and Fe.
    Type: Application
    Filed: March 11, 2014
    Publication date: January 28, 2016
    Applicant: Rutgars, The State University of New Jersey
    Inventor: Xumu Zhang
  • Patent number: 7714149
    Abstract: The present invention provides a chiral ligand, represented by a formula or its enantiomer: X and X? can be independently O, NH, NR, NCOR or S; each of Z1-Z7 and Z1?-Z7? can be independently H, alkyl, aryl, substituted alkyl, substituted aryl, alkoxyl, aryloxyl, nitro, amide, aryoxide, halide, hydroxyl, carboxylate, hetereoaryl, or a cyclic alkene, fused aryl, or cyclic ether group formed from any two adjacent Z groups or any two adjacent Z? groups; Y and Y? can be independently OH, OR, NH2, NHR, NR2, SH, PR2, OPR2, NHPR2, OP(OR)2, COOH, COOR, CONHR, or a linking group formed from Y and Y? groups together. Processes of preparing these ligands, catalysts that employ them and methods of using the catalysts are also provided.
    Type: Grant
    Filed: September 1, 2005
    Date of Patent: May 11, 2010
    Assignee: The Penn State Research Foundation
    Inventor: Xumu Zhang
  • Patent number: 7709655
    Abstract: Phosphine triazole ligand compounds, prepared through click chemistry, complex with transition metals to form transition metal-phosphine triazole ligand complexes. These complexes are useful catalysts in coupling reactions such as Suzuki-Miyaura coupling, Stille coupling, Negishi coupling, Sonagashira coupling, carbon-heteroatom bond-forming reactions (C—O and C—N), alpha alkylation of carbonyls, Heck coupling reactions, and hydrogenation reactions.
    Type: Grant
    Filed: June 2, 2006
    Date of Patent: May 4, 2010
    Assignee: The Penn State Research Foundation
    Inventor: Xumu Zhang
  • Patent number: 7709659
    Abstract: Tetraphosphorous ligands are combined with transition metal salts to form catalysts for use in hydroformylation, isomerization-hydroformylation, hydrocarboxylation, hydrocyan-ation, isomerization-formylation, hydroaminomethylation and similar related reactions.
    Type: Grant
    Filed: April 17, 2009
    Date of Patent: May 4, 2010
    Assignee: The Penn State Research Foundation
    Inventors: Xumu Zhang, Yongjun Yan
  • Patent number: 7589218
    Abstract: The present invention provides a chiral ligand, represented by a formula or its enantiomer: X and X? can be independently O, NH, NR, NCOR or S; each of Z1-Z7 and Z1?-Z7? can be independently H, alkyl, aryl, substituted alkyl, substituted aryl, alkoxyl, aryloxyl, nitro, amide, aryloxide, halide, hydroxyl, carboxylate, heteroaryl, or a cyclic alkene, fused aryl, or cyclic ether group formed from any two adjacent Z groups or any two adjacent Z? groups; Y and Y? can be independently OH, OR, NH2, NHR, NR2, SH, PR2, OPR2, NHPR2, OP(OR)2, COOH, COOR, CONHR, or a linking group formed from Y and Y? groups together. Processes of preparing these ligands, catalysts that employ them and methods of using the catalysts are also provided.
    Type: Grant
    Filed: July 15, 2008
    Date of Patent: September 15, 2009
    Assignee: The Penn State Research Foundation
    Inventor: Xumu Zhang
  • Publication number: 20090198071
    Abstract: Tetraphosphorous ligands are combined with transition metal salts to form catalysts for use in hydroformylation, isomerization-hydroformylation, hydrocarboxylation, hydrocyan-ation, isomerization-formylation, hydroaminomethylation and similar related reactions.
    Type: Application
    Filed: April 17, 2009
    Publication date: August 6, 2009
    Applicant: THE PENN STATE RESEARCH FOUNDATION
    Inventors: Xumu ZHANG, Yongjun Yan
  • Patent number: 7538228
    Abstract: A chiral ligand represented by the formula and its enantiomer: wherein A, X, Y and Z are as defined in the specification is provided. Also provided is a process of making the chiral ligands and catalysts prepared from these ligands and a transition metal, a salt thereof or a complex thereof. In addition, a method of preparing an asymmetric compound by a transition metal catalyzed asymmetric reaction, such as, hydrogenation, hydride transfer reaction, hydrosilylation, hydroboration, hydrovinylation, hydroformylation, hydrocarboxylation, allylic alkylation, epoxidation, cyclopropanation, Diels-Alder reaction, Aldol reaction, ene reaction, Heck reaction and Michael addition is provided.
    Type: Grant
    Filed: December 17, 2004
    Date of Patent: May 26, 2009
    Assignee: The Penn State Research Foundation
    Inventors: Xumu Zhang, Duan Liu
  • Patent number: 7531698
    Abstract: Tetraphosphorous ligands are combined with transition metal salts to form catalysts for use in hydroformylation, isomerization-hydroformylation, hydrocarboxylation, hydrocyan-ation, isomerization-formylation, hydroaminomethylation and similar related reactions.
    Type: Grant
    Filed: December 15, 2006
    Date of Patent: May 12, 2009
    Assignee: The Penn State Research Foundation
    Inventors: Xumu Zhang, Yongjun Yan
  • Publication number: 20080293953
    Abstract: The present invention provides a chiral ligand, represented by a formula or its enantiomer: X and X? can be independently O, NH, NR, NCOR or S; each of Z1-Z7 and Z1?-Z7? can be independently H, alkyl, aryl, substituted alkyl, substituted aryl, alkoxyl, aryloxyl, nitro, amide, aryloxide, halide, hydroxyl, carboxylate, heteroaryl, or a cyclic alkene, fused aryl, or cyclic ether group formed from any two adjacent Z groups or any two adjacent Z? groups; Y and Y? can be independently OH, OR, NH2, NHR, NR2, SH, PR2, OPR2, NHPR2, OP(OR)2, COOH, COOR, CONHR, or a linking group formed from Y and Y? groups together. Processes of preparing these ligands, catalysts that employ them and methods of using the catalysts are also provided.
    Type: Application
    Filed: July 15, 2008
    Publication date: November 27, 2008
    Applicant: The Penn State Research Foundation
    Inventor: Xumu Zhang
  • Publication number: 20070203365
    Abstract: Tetraphosphorous ligands are combined with transition metal salts to form catalysts for use in hydroformylation, isomerization-hydroformylation, hydrocarboxylation, hydrocyan-ation, isomerization-formylation, hydroaminomethylation and similar related reactions.
    Type: Application
    Filed: December 15, 2006
    Publication date: August 30, 2007
    Inventors: Xumu Zhang, Yongjun Yan
  • Patent number: 7214813
    Abstract: Cyclic ?-(acylamino)acrylate derivatives were hydrogenated using Ru-chiral phosphine ligand catalysts and thereafter converted to the corresponding cyclic ?-aminoacids in high yield and enantioselectivity according to the reaction scheme:
    Type: Grant
    Filed: May 27, 2004
    Date of Patent: May 8, 2007
    Assignee: The Penn State Research Foundation
    Inventors: Xumu Zhang, Wenjun Tang
  • Publication number: 20070088166
    Abstract: Phosphine triazole ligand compounds, prepared through click chemistry, complex with transition metals to form transition metal-phosphine triazole ligand complexes. These complexes are useful catalysts in coupling reactions such as Suzuki-Miyaura coupling, Stille coupling, Negishi coupling, Sonagashira coupling, carbon-heteroatom bond-forming reactions (C—O and C—N), alpha alkylation of carbonyls, Heck coupling reactions, and hydrogenation reactions.
    Type: Application
    Filed: June 2, 2006
    Publication date: April 19, 2007
    Inventor: Xumu Zhang
  • Patent number: 7169953
    Abstract: Chiral ligands and metal complexes based on such chiral ligands useful in asymmetric catalysis are disclosed. The metal complexes according to the present invention are useful as catalysts in asymmetric reactions, such as, hydrogenation, hydride transfer, allylic alkylation, hydrosilylation, hydroboration, hydrovinylation, hydroformylation, olefin metathesis, hydrocarboxylation, isomerization, cyclopropanation, Diels-Alder reaction, Heck reaction, isomerization, Aldol reaction, Michael addition; epoxidation, kinetic resolution and [m+n] cycloaddition. Processes for the preparation of the ligands are also described.
    Type: Grant
    Filed: May 28, 2004
    Date of Patent: January 30, 2007
    Assignee: The Penn State Research Foundation
    Inventors: Xumu Zhang, Wenjun Tang