Title:
MECHANOCHEMICAL REACTION ADDITIVE, MECHANOCHEMICAL METHOD, LIGAND COMPOUND, AND COMPLEX
Document Type and Number:
WIPO Patent Application WO/2023/167321
Kind Code:
A1
Abstract:
The present invention addresses the problem of providing mechanochemical reaction additive that can be handled in air, that can be easily synthesized, that when used in a mechanochemical reaction can increase the activity of the mechanochemical reaction, and that can be applied to a wide variety of substrates under gentle conditions. Provided as a solution is a mechanochemical reaction additive comprising at least a ligand compound (Lx) or a salt thereof, wherein the ligand compound (Lx) is one or more compounds from among phosphorus-based compounds, bipyridine compounds, and N-heterocyclic carbene-based compounds, the ligand compound (Lx) has a polymer chain in the molecule thereof, and the polymer chain is one or more polymer chains from among polyethers, polyamides, polyesters, and polyurethanes.
Inventors:
ITO HAJIME (JP)
KUBOTA KOJI (JP)
KUBOTA KOJI (JP)
Application Number:
PCT/JP2023/008125
Publication Date:
September 07, 2023
Filing Date:
March 03, 2023
Export Citation:
Assignee:
UNIV HOKKAIDO NAT UNIV CORP (JP)
International Classes:
C07B61/00; C07B37/04; C07C41/30; C07C43/20; C07C43/205; C07C43/21; C07C43/215; C07C45/68; C07C49/517; C07C49/84; C07F9/50; C08G65/327
Domestic Patent References:
| WO2017172462A1 | 2017-10-05 | |||
| WO2020009016A1 | 2020-01-09 | |||
| WO2013121997A1 | 2013-08-22 | |||
| WO2003066548A2 | 2003-08-14 |
Foreign References:
| CN109336924A | 2019-02-15 | |||
| US20100143464A1 | 2010-06-10 | |||
| US5990318A | 1999-11-23 | |||
| JP2016098194A | 2016-05-30 | |||
| US20140275555A1 | 2014-09-18 |
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PORNCHAI KAEWSAPSAK; ONYINYECHI ESONU; DANIELLE H. DUBE: "Recruiting the Host's Immune System to Target Helicobacter pylori's Surface Glycans", CHEMBIOCHEM, JOHN WILEY & SONS, INC., HOBOKEN, USA, vol. 14, no. 6, 19 March 2013 (2013-03-19), Hoboken, USA, pages 721 - 726, XP072150243, ISSN: 1439-4227, DOI: 10.1002/cbic.201300006
FUJIHARA TETSUAKI, YOSHIDA SHOHEI, TERAO JUN, TSUJI YASUSHI: "A Triarylphosphine Ligand Bearing Dodeca(ethylene glycol) Chains: Enhanced Efficiency in the Palladium-Catalyzed Suzuki−Miyaura Coupling Reaction", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, US, vol. 11, no. 10, 21 May 2009 (2009-05-21), US , pages 2121 - 2124, XP093088547, ISSN: 1523-7060, DOI: 10.1021/ol900578g
SØRENSEN HANNE S., LARSEN JENS, RASMUSSEN BRIAN S., LAURSEN BOLETTE, HANSEN SIGNE G., SKRYDSTRUP TROELS, AMATORE CHRISTIAN, JUTAND: "Synthesis and Investigation of New Macrocyclic Diphosphine−Palladium(0) Complexes Based on the Barbiturate Binding Receptor", ORGANOMETALLICS, AMERICAN CHEMICAL SOCIETY, vol. 21, no. 24, 1 November 2002 (2002-11-01), pages 5243 - 5253, XP093088548, ISSN: 0276-7333, DOI: 10.1021/om020364v
WANG, YANHUA; JIANG, JINGYANG; MIAO, QIANG; WU, XIAOWEI; JIN, ZILIN: "Thermoregulated phase transfer ligands and catalysis. Part XIII. Use of nonionic tensioactive water - soluble phosphine ligands to effect homogeneous catalyst separation and recycling", CATALYSIS TODAY, ELSEVIER, AMSTERDAM, NL, vol. 74, no. 1-2, 1 January 2002 (2002-01-01), AMSTERDAM, NL , pages 85 - 90, XP009127755, ISSN: 0920-5861, DOI: 10.1016/S0920-5861(01)00533-8
TAIRA TOSHIAKI, YANAGIMOTO TAKAYA, FOUQUET THIERRY, SAKAI KENICHI, SAKAI HIDEKI, IMURA TOMOHIRO: "Synthesis of an N-Heterocyclic Carbene-based Au(I) Coordinate Surfactant: Application for Alkyne Hydration Based on Au Nanoparticle Formation", JOURNAL OF OLEO SCIENCE, JAPAN OIL CHEMISTS SOCIETY, TOKYO, JP, vol. 69, no. 8, 1 January 2020 (2020-01-01), JP , pages 871 - 882, XP093088552, ISSN: 1345-8957, DOI: 10.5650/jos.ess20063
GUPTA AJAY, PRASAD PUJA, GUPTA SHALINI, SASMAL PIJUS K.: "Simultaneous Ultrasensitive Detection and Elimination of Drug-Resistant Bacteria by Cyclometalated Iridium(III) Complexes", APPLIED MATERIALS & INTERFACES, AMERICAN CHEMICAL SOCIETY, US, vol. 12, no. 32, 12 August 2020 (2020-08-12), US , pages 35967 - 35976, XP093088553, ISSN: 1944-8244, DOI: 10.1021/acsami.0c11161
DAHM GEORGES; BOUCHé MATHILDE; BAILLY CORINNE; KARMAZIN LYDIA; BELLEMIN-LAPONNAZ STéPHANE: "Synthesis and structural characterization of benzyl-functionalized N-heterocyclic carbene platinum complexes: Dramatic substituent effect on anti-cancer activity", JOURNAL OF ORGANOMETALLIC CHEMISTRY, ELSEVIER, AMSTERDAM, NL, vol. 899, 21 August 2019 (2019-08-21), AMSTERDAM, NL , XP085814745, ISSN: 0022-328X, DOI: 10.1016/j.jorganchem.2019.120908
AKIO URUSHIMA; NAOKI OUSAKA; EIJI YASHIMA: "Tug‐of‐War in a Dynamic Helical Peptide: Solvent‐Induced Helix‐Helix Transition of a Lactam‐Bridged Peptide Composed of Point‐ and Axial Chiralities Remote from Each Other", CHEMISTRY - AN ASIAN JOURNAL, WILEY-VCH, HOBOKEN, USA, vol. 13, no. 21, 4 September 2018 (2018-09-04), Hoboken, USA, pages 3150 - 3154, XP072428876, ISSN: 1861-4728, DOI: 10.1002/asia.201801111
KIM CHEOLJAE, CHUNG HOYONG: "Oligo(ethylene glycol) Length Effect of Water-Soluble Ru-Based Olefin Metathesis Catalysts on Reactivity and Removability", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 83, no. 17, 7 September 2018 (2018-09-07), pages 9787 - 9794, XP093088555, ISSN: 0022-3263, DOI: 10.1021/acs.joc.8b01312
FUJITA KEN-ICHI; INOUE KENSUKE; SATO JUNICHI; TSUCHIMOTO TERUHISA; YASUDA HIROYUKI: "Carboxylative cyclization of propargylic amines with CO2catalyzed by dendritic N-heterocyclic carbene–gold(I) complexes", TETRAHEDRON, ELSEVIER SIENCE PUBLISHERS, AMSTERDAM, NL, vol. 72, no. 9, 11 January 2016 (2016-01-11), AMSTERDAM, NL , pages 1205 - 1212, XP029408308, ISSN: 0040-4020, DOI: 10.1016/j.tet.2016.01.016
YAM VIVIAN WING-WAH, SONG HAI-OU, CHAN STEVE TAK-WAH, ZHU NIANYONG, TAO CHI-HANG, WONG KEITH MAN-CHUNG, WU LI-XIN: "Synthesis, Characterization, Ion-Binding Properties, and Fluorescence Resonance Energy Transfer Behavior of Rhenium(I) Complexes Containing a Coumarin-Appended 2,2′-Bipyridine", THE JOURNAL OF PHYSICAL CHEMISTRY C, AMERICAN CHEMICAL SOCIETY, US, vol. 113, no. 27, 9 July 2009 (2009-07-09), US , pages 11674 - 11682, XP093088556, ISSN: 1932-7447, DOI: 10.1021/jp901561v
GINA L. FIORE, CASSANDRA L. FRASER: "Iron-Centered Star Polymers with Pentablock Bipyridine-Centered PEG-PCL-PLA Macroligands", MACROMOLECULES, AMERICAN CHEMICAL SOCIETY, US, vol. 41, no. 21, 11 November 2008 (2008-11-11), US , pages 7892 - 7897, XP055319881, ISSN: 0024-9297, DOI: 10.1021/ma801353b
MEISE MARKUS, HAAG RAINER: "A Highly Active Water‐Soluble Cross‐Coupling Catalyst Based on Dendritic Polyglycerol N‐Heterocyclic Carbene Palladium Complexes", CHEMSUSCHEM, WILEY-VCH, DE, vol. 1, no. 7, 21 July 2008 (2008-07-21), DE , pages 637 - 642, XP093088558, ISSN: 1864-5631, DOI: 10.1002/cssc.200800042
RICHARD ANTOINE, MARCHI-ARTZNER VALÉRIE, LALLOZ MARIE-NOËLLE, BRIENNE MARIE-JOSÈPHE, ARTZNER FRANCK, GULIK-KRZYWICKI THADDÉE, GUED: "Fusogenic supramolecular vesicle systems induced by metal ion binding to amphiphilic ligands", PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES, NATIONAL ACADEMY OF SCIENCES, vol. 101, no. 43, 26 October 2004 (2004-10-26), pages 15279 - 15284, XP093088927, ISSN: 0027-8424, DOI: 10.1073/pnas.0406625101
PORNCHAI KAEWSAPSAK; ONYINYECHI ESONU; DANIELLE H. DUBE: "Recruiting the Host's Immune System to Target Helicobacter pylori's Surface Glycans", CHEMBIOCHEM, JOHN WILEY & SONS, INC., HOBOKEN, USA, vol. 14, no. 6, 19 March 2013 (2013-03-19), Hoboken, USA, pages 721 - 726, XP072150243, ISSN: 1439-4227, DOI: 10.1002/cbic.201300006
FUJIHARA TETSUAKI, YOSHIDA SHOHEI, TERAO JUN, TSUJI YASUSHI: "A Triarylphosphine Ligand Bearing Dodeca(ethylene glycol) Chains: Enhanced Efficiency in the Palladium-Catalyzed Suzuki−Miyaura Coupling Reaction", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, US, vol. 11, no. 10, 21 May 2009 (2009-05-21), US , pages 2121 - 2124, XP093088547, ISSN: 1523-7060, DOI: 10.1021/ol900578g
SØRENSEN HANNE S., LARSEN JENS, RASMUSSEN BRIAN S., LAURSEN BOLETTE, HANSEN SIGNE G., SKRYDSTRUP TROELS, AMATORE CHRISTIAN, JUTAND: "Synthesis and Investigation of New Macrocyclic Diphosphine−Palladium(0) Complexes Based on the Barbiturate Binding Receptor", ORGANOMETALLICS, AMERICAN CHEMICAL SOCIETY, vol. 21, no. 24, 1 November 2002 (2002-11-01), pages 5243 - 5253, XP093088548, ISSN: 0276-7333, DOI: 10.1021/om020364v
WANG, YANHUA; JIANG, JINGYANG; MIAO, QIANG; WU, XIAOWEI; JIN, ZILIN: "Thermoregulated phase transfer ligands and catalysis. Part XIII. Use of nonionic tensioactive water - soluble phosphine ligands to effect homogeneous catalyst separation and recycling", CATALYSIS TODAY, ELSEVIER, AMSTERDAM, NL, vol. 74, no. 1-2, 1 January 2002 (2002-01-01), AMSTERDAM, NL , pages 85 - 90, XP009127755, ISSN: 0920-5861, DOI: 10.1016/S0920-5861(01)00533-8
TAIRA TOSHIAKI, YANAGIMOTO TAKAYA, FOUQUET THIERRY, SAKAI KENICHI, SAKAI HIDEKI, IMURA TOMOHIRO: "Synthesis of an N-Heterocyclic Carbene-based Au(I) Coordinate Surfactant: Application for Alkyne Hydration Based on Au Nanoparticle Formation", JOURNAL OF OLEO SCIENCE, JAPAN OIL CHEMISTS SOCIETY, TOKYO, JP, vol. 69, no. 8, 1 January 2020 (2020-01-01), JP , pages 871 - 882, XP093088552, ISSN: 1345-8957, DOI: 10.5650/jos.ess20063
GUPTA AJAY, PRASAD PUJA, GUPTA SHALINI, SASMAL PIJUS K.: "Simultaneous Ultrasensitive Detection and Elimination of Drug-Resistant Bacteria by Cyclometalated Iridium(III) Complexes", APPLIED MATERIALS & INTERFACES, AMERICAN CHEMICAL SOCIETY, US, vol. 12, no. 32, 12 August 2020 (2020-08-12), US , pages 35967 - 35976, XP093088553, ISSN: 1944-8244, DOI: 10.1021/acsami.0c11161
DAHM GEORGES; BOUCHé MATHILDE; BAILLY CORINNE; KARMAZIN LYDIA; BELLEMIN-LAPONNAZ STéPHANE: "Synthesis and structural characterization of benzyl-functionalized N-heterocyclic carbene platinum complexes: Dramatic substituent effect on anti-cancer activity", JOURNAL OF ORGANOMETALLIC CHEMISTRY, ELSEVIER, AMSTERDAM, NL, vol. 899, 21 August 2019 (2019-08-21), AMSTERDAM, NL , XP085814745, ISSN: 0022-328X, DOI: 10.1016/j.jorganchem.2019.120908
AKIO URUSHIMA; NAOKI OUSAKA; EIJI YASHIMA: "Tug‐of‐War in a Dynamic Helical Peptide: Solvent‐Induced Helix‐Helix Transition of a Lactam‐Bridged Peptide Composed of Point‐ and Axial Chiralities Remote from Each Other", CHEMISTRY - AN ASIAN JOURNAL, WILEY-VCH, HOBOKEN, USA, vol. 13, no. 21, 4 September 2018 (2018-09-04), Hoboken, USA, pages 3150 - 3154, XP072428876, ISSN: 1861-4728, DOI: 10.1002/asia.201801111
KIM CHEOLJAE, CHUNG HOYONG: "Oligo(ethylene glycol) Length Effect of Water-Soluble Ru-Based Olefin Metathesis Catalysts on Reactivity and Removability", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 83, no. 17, 7 September 2018 (2018-09-07), pages 9787 - 9794, XP093088555, ISSN: 0022-3263, DOI: 10.1021/acs.joc.8b01312
FUJITA KEN-ICHI; INOUE KENSUKE; SATO JUNICHI; TSUCHIMOTO TERUHISA; YASUDA HIROYUKI: "Carboxylative cyclization of propargylic amines with CO2catalyzed by dendritic N-heterocyclic carbene–gold(I) complexes", TETRAHEDRON, ELSEVIER SIENCE PUBLISHERS, AMSTERDAM, NL, vol. 72, no. 9, 11 January 2016 (2016-01-11), AMSTERDAM, NL , pages 1205 - 1212, XP029408308, ISSN: 0040-4020, DOI: 10.1016/j.tet.2016.01.016
YAM VIVIAN WING-WAH, SONG HAI-OU, CHAN STEVE TAK-WAH, ZHU NIANYONG, TAO CHI-HANG, WONG KEITH MAN-CHUNG, WU LI-XIN: "Synthesis, Characterization, Ion-Binding Properties, and Fluorescence Resonance Energy Transfer Behavior of Rhenium(I) Complexes Containing a Coumarin-Appended 2,2′-Bipyridine", THE JOURNAL OF PHYSICAL CHEMISTRY C, AMERICAN CHEMICAL SOCIETY, US, vol. 113, no. 27, 9 July 2009 (2009-07-09), US , pages 11674 - 11682, XP093088556, ISSN: 1932-7447, DOI: 10.1021/jp901561v
GINA L. FIORE, CASSANDRA L. FRASER: "Iron-Centered Star Polymers with Pentablock Bipyridine-Centered PEG-PCL-PLA Macroligands", MACROMOLECULES, AMERICAN CHEMICAL SOCIETY, US, vol. 41, no. 21, 11 November 2008 (2008-11-11), US , pages 7892 - 7897, XP055319881, ISSN: 0024-9297, DOI: 10.1021/ma801353b
MEISE MARKUS, HAAG RAINER: "A Highly Active Water‐Soluble Cross‐Coupling Catalyst Based on Dendritic Polyglycerol N‐Heterocyclic Carbene Palladium Complexes", CHEMSUSCHEM, WILEY-VCH, DE, vol. 1, no. 7, 21 July 2008 (2008-07-21), DE , pages 637 - 642, XP093088558, ISSN: 1864-5631, DOI: 10.1002/cssc.200800042
RICHARD ANTOINE, MARCHI-ARTZNER VALÉRIE, LALLOZ MARIE-NOËLLE, BRIENNE MARIE-JOSÈPHE, ARTZNER FRANCK, GULIK-KRZYWICKI THADDÉE, GUED: "Fusogenic supramolecular vesicle systems induced by metal ion binding to amphiphilic ligands", PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES, NATIONAL ACADEMY OF SCIENCES, vol. 101, no. 43, 26 October 2004 (2004-10-26), pages 15279 - 15284, XP093088927, ISSN: 0027-8424, DOI: 10.1073/pnas.0406625101
Attorney, Agent or Firm:
YAMADA, Yasuyuki et al. (JP)
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