ITUB20160229A1 - Monocarbonyl ruthenium and osmium catalysts - Google Patents

Monocarbonyl ruthenium and osmium catalysts

Info

Publication number
ITUB20160229A1
ITUB20160229A1 ITUB2016A000229A ITUB20160229A ITUB20160229A1 IT UB20160229 A1 ITUB20160229 A1 IT UB20160229A1 IT UB2016A000229 A ITUB2016A000229 A IT UB2016A000229A IT UB20160229 A ITUB20160229 A IT UB20160229A IT UB20160229 A1 ITUB20160229 A1 IT UB20160229A1
Authority
IT
Italy
Prior art keywords
monocarbonyl
ruthenium
osmium catalysts
osmium
catalysts
Prior art date
Application number
ITUB2016A000229A
Other languages
English (en)
Inventor
Walter Baratta
Salvatore Baldino
Steven Giboulot
Original Assignee
Univ Degli Studi Udine
Innovation Factory S R L
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Univ Degli Studi Udine, Innovation Factory S R L filed Critical Univ Degli Studi Udine
Priority to ITUB2016A000229A priority Critical patent/ITUB20160229A1/it
Priority to JP2018541274A priority patent/JP6923542B2/ja
Priority to EP17706312.0A priority patent/EP3411347B1/en
Priority to CN201780018674.6A priority patent/CN108779042B/zh
Priority to GB1814431.1A priority patent/GB2565443B/en
Priority to PCT/IB2017/050598 priority patent/WO2017134618A1/en
Priority to US16/075,315 priority patent/US11278876B2/en
Publication of ITUB20160229A1 publication Critical patent/ITUB20160229A1/it
Priority to US17/673,220 priority patent/US11577233B2/en
Priority to US18/150,909 priority patent/US11819837B2/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B41/00—Formation or introduction of functional groups containing oxygen
    • C07B41/02—Formation or introduction of functional groups containing oxygen of hydroxy or O-metal groups
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B01J31/2442—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems
    • B01J31/2447—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as substituents on a ring of the condensed system or on a further attached ring
    • B01J31/2452—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as substituents on a ring of the condensed system or on a further attached ring with more than one complexing phosphine-P atom
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
    • B01J31/1815—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine
    • B01J31/182—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine comprising aliphatic or saturated rings
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/189—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms containing both nitrogen and phosphorus as complexing atoms, including e.g. phosphino moieties, in one at least bidentate or bridging ligand
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B01J31/2419—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising P as ring member
    • B01J31/2428—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising P as ring member with more than one complexing phosphine-P atom
    • B01J31/2433—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising P as ring member with more than one complexing phosphine-P atom comprising aliphatic or saturated rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
    • C07C29/145—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones with hydrogen or hydrogen-containing gases
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
    • C07F15/002—Osmium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
    • C07F15/0046—Ruthenium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
    • C07F15/0046—Ruthenium compounds
    • C07F15/0053—Ruthenium compounds without a metal-carbon linkage
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/60—Reduction reactions, e.g. hydrogenation
    • B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
    • B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0238—Complexes comprising multidentate ligands, i.e. more than 2 ionic or coordinative bonds from the central metal to the ligand, the latter having at least two donor atoms, e.g. N, O, S, P
    • B01J2531/0241—Rigid ligands, e.g. extended sp2-carbon frameworks or geminal di- or trisubstitution
    • B01J2531/0244—Pincer-type complexes, i.e. consisting of a tridentate skeleton bound to a metal, e.g. by one to three metal-carbon sigma-bonds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/821—Ruthenium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/825—Osmium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
ITUB2016A000229A 2016-02-05 2016-02-05 Monocarbonyl ruthenium and osmium catalysts ITUB20160229A1 (it)

Priority Applications (9)

Application Number Priority Date Filing Date Title
ITUB2016A000229A ITUB20160229A1 (it) 2016-02-05 2016-02-05 Monocarbonyl ruthenium and osmium catalysts
JP2018541274A JP6923542B2 (ja) 2016-02-05 2017-02-03 モノカルボニルルテニウム触媒及びモノカルボニルオスミウム触媒
EP17706312.0A EP3411347B1 (en) 2016-02-05 2017-02-03 Monocarbonyl ruthenium and osmium catalysts
CN201780018674.6A CN108779042B (zh) 2016-02-05 2017-02-03 单羰基钌和锇催化剂
GB1814431.1A GB2565443B (en) 2016-02-05 2017-02-03 Monocarbonyl ruthenium and osmium catalysts
PCT/IB2017/050598 WO2017134618A1 (en) 2016-02-05 2017-02-03 Monocarbonyl ruthenium and osmium catalysts
US16/075,315 US11278876B2 (en) 2016-02-05 2017-02-03 Monocarbonyl ruthenium and osmium catalysts
US17/673,220 US11577233B2 (en) 2016-02-05 2022-02-16 Monocarbonyl ruthenium and osmium catalysts
US18/150,909 US11819837B2 (en) 2016-02-05 2023-01-06 Monocarbonyl ruthenium and osmium catalysts

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
ITUB2016A000229A ITUB20160229A1 (it) 2016-02-05 2016-02-05 Monocarbonyl ruthenium and osmium catalysts

Publications (1)

Publication Number Publication Date
ITUB20160229A1 true ITUB20160229A1 (it) 2017-08-05

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Family Applications (1)

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ITUB2016A000229A ITUB20160229A1 (it) 2016-02-05 2016-02-05 Monocarbonyl ruthenium and osmium catalysts

Country Status (7)

Country Link
US (3) US11278876B2 (it)
EP (1) EP3411347B1 (it)
JP (1) JP6923542B2 (it)
CN (1) CN108779042B (it)
GB (1) GB2565443B (it)
IT (1) ITUB20160229A1 (it)
WO (1) WO2017134618A1 (it)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109776610B (zh) * 2017-11-14 2021-05-14 中国科学院大连化学物理研究所 基于苯乙胺骨架的手性p,n,n配体类化合物及制备方法与应用
EP3994117A1 (de) 2019-07-03 2022-05-11 Basf Se Hydrierung von estern zu alkoholen in gegenwart eines ru-pnn-komplexes

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005051965A2 (en) * 2003-11-26 2005-06-09 Universita' Degli Studi Di Udine Ruthenium complexes, their preparation and use as catalysts

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GB9217811D0 (en) 1992-08-21 1992-10-07 Graetzel Michael Organic compounds
FI98603C (fi) 1995-11-09 1997-07-25 Neste Oy Menetelmä vesikaasun siirtoreaktiokatalyyttien valmistamiseksi ja katalyytin käyttö
AU2003304324A1 (en) * 2003-07-14 2005-01-28 Fernando De Buen Unna Road signal for vehicles parked for emergency reasons
ITPD20070237A1 (it) 2007-07-11 2009-01-12 Univ Degli Studi Udine Nuovi leganti della classe della benzo[h]chinolina e complessi di metalli di transizione che li contengono e uso di tali complessi come catalizzatori
WO2011048727A1 (ja) * 2009-10-23 2011-04-28 高砂香料工業株式会社 ３座配位子を有する新規ルテニウムカルボニル錯体、並びにその製造法及び用途
GB201104522D0 (en) 2011-03-17 2011-05-04 Johnson Matthey Plc Complexes

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Publication number Priority date Publication date Assignee Title
WO2005051965A2 (en) * 2003-11-26 2005-06-09 Universita' Degli Studi Di Udine Ruthenium complexes, their preparation and use as catalysts

Non-Patent Citations (4)

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Title
BARUN BERA ET AL: "Dynamics of H-atom exchange in stable cis-dihydrogen/hydride complexes of ruthenium(ii) bearing phosphine and N-N bidentate ligands", DALTON TRANSACTIONS: THE INTERNATIONAL JOURNAL FOR INORGANIC, ORGANOMETALLIC AND BIOINORGANIC CHEMISTRY, vol. 43, no. 12, 1 January 2014 (2014-01-01), GB, pages 4726, XP055297938, ISSN: 1477-9226, DOI: 10.1039/c3dt52575a *
CAVARZAN DEIVIDI ALEXANDRE ET AL: "Neutral and cationic ruthenium carbonyl complexes [Ru(CO)(2,2'-dipyridylamine)(PR3)Cl2] and [Ru(CO)(N-N)(PPh3)2(H)]Cl: synthesis, structural characterization and transfer-hydrogena", TRANSITION METAL CHEMISTRY, CHAPMAN & HALL, GB, vol. 40, no. 1, 31 October 2014 (2014-10-31), pages 117 - 123, XP035432807, ISSN: 0340-4285, [retrieved on 20141031], DOI: 10.1007/S11243-014-9896-8 *
PRASHANT KUMAR ET AL: "Synthesis and characterization of ruthenium(II) complexes based on diphenyl-2-pyridylphosphine and their applications in transfer hydrogenation of ketones", INORGANICA CHIMICA ACTA, ELSEVIER BV, NL, vol. 368, no. 1, 21 December 2010 (2010-12-21), pages 124 - 131, XP028182335, ISSN: 0020-1693, [retrieved on 20101230], DOI: 10.1016/J.ICA.2010.12.057 *
THANGAVEL SATHIYA KAMATCHI ET AL: "Influence of carboxylic acid functionalities in ruthenium (II) polypyridyl complexes on DNA binding, cytotoxicity and antioxidant activity: Synthesis, structure and in vitro anticancer activity", EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY., vol. 59, 1 January 2013 (2013-01-01), FR, pages 253 - 264, XP055297941, ISSN: 0223-5234, DOI: 10.1016/j.ejmech.2012.11.024 *

Also Published As

Publication number Publication date
GB201814431D0 (en) 2018-10-17
EP3411347B1 (en) 2021-03-31
JP2019507140A (ja) 2019-03-14
CN108779042A (zh) 2018-11-09
GB2565443A (en) 2019-02-13
US11577233B2 (en) 2023-02-14
WO2017134618A1 (en) 2017-08-10
US20220168720A1 (en) 2022-06-02
EP3411347A1 (en) 2018-12-12
US11819837B2 (en) 2023-11-21
US20190030522A1 (en) 2019-01-31
GB2565443B (en) 2022-04-06
CN108779042B (zh) 2022-07-19
US11278876B2 (en) 2022-03-22
US20230145668A1 (en) 2023-05-11
JP6923542B2 (ja) 2021-08-18

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