CA2653150C - Chiral ligands used in transition metal catalysts for asymmetric addition reactions especially hydrogenation - Google Patents

Chiral ligands used in transition metal catalysts for asymmetric addition reactions especially hydrogenation Download PDF

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CA2653150C
CA2653150C CA2653150A CA2653150A CA2653150C CA 2653150 C CA2653150 C CA 2653150C CA 2653150 A CA2653150 A CA 2653150A CA 2653150 A CA2653150 A CA 2653150A CA 2653150 C CA2653150 C CA 2653150C
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alkyl
alkoxy
compound
formula
radical
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French (fr)
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CA2653150A1 (en
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Andreas Pfaltz
Yann Ribourdouille
Xiangdong Feng
Balamurugan Ramalingam
Benoit Pugin
Felix Spindler
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Solvias AG
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Solvias AG
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/28Phosphorus compounds with one or more P—C bonds
    • C07F9/50Organo-phosphines
    • C07F9/5022Aromatic phosphines (P-C aromatic linkage)
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18Catalysts 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
    • B01J31/1845Catalysts 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 phosphorus
    • B01J31/1875Phosphinites (R2P(OR), their isomeric phosphine oxides (R3P=O) and RO-substitution derivatives thereof)
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24Phosphines, 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
    • B01J31/2495Ligands comprising a phosphine-P atom and one or more further complexing phosphorus atoms covered by groups B01J31/1845 - B01J31/1885, e.g. phosphine/phosphinate or phospholyl/phosphonate ligands
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/02Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00Preparation of carboxylic acid amides
    • C07C231/12Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/36Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by hydrogenation of carbon-to-carbon unsaturated bonds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/30Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/303Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by hydrogenation of unsaturated carbon-to-carbon bonds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0073Rhodium compounds
    • C07F15/008Rhodium compounds without a metal-carbon linkage
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F17/00Metallocenes
    • C07F17/02Metallocenes of metals of Groups 8, 9 or 10 of the Periodic Table
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/60Reduction reactions, e.g. hydrogenation
    • B01J2231/64Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
    • B01J2231/641Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
    • B01J2231/643Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of R2C=O or R2C=NR (R= C, H)
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/60Reduction reactions, e.g. hydrogenation
    • B01J2231/64Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
    • B01J2231/641Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
    • B01J2231/645Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of C=C or C-C triple bonds
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82Metals of the platinum group
    • B01J2531/821Ruthenium
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82Metals of the platinum group
    • B01J2531/822Rhodium
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82Metals of the platinum group
    • B01J2531/827Iridium
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07Optical isomers

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Inorganic Chemistry (AREA)
  • Materials Engineering (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
CA2653150A 2006-05-23 2007-05-23 Chiral ligands used in transition metal catalysts for asymmetric addition reactions especially hydrogenation Active CA2653150C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH8312006 2006-05-23
CH00831/806 2006-05-23
PCT/EP2007/055026 WO2007135179A1 (en) 2006-05-23 2007-05-23 Chiral ligands used in transition metal catalysts for asymmetric addition reactions especially hydrogenation

Publications (2)

Publication Number Publication Date
CA2653150A1 CA2653150A1 (en) 2007-11-29
CA2653150C true CA2653150C (en) 2014-05-13

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Family Applications (1)

Application Number Title Priority Date Filing Date
CA2653150A Active CA2653150C (en) 2006-05-23 2007-05-23 Chiral ligands used in transition metal catalysts for asymmetric addition reactions especially hydrogenation

Country Status (8)

Country Link
US (1) US8008529B2 (https=)
EP (1) EP2027134B1 (https=)
JP (1) JP5209611B2 (https=)
CN (1) CN101448845B (https=)
CA (1) CA2653150C (https=)
ES (1) ES2493634T3 (https=)
IL (1) IL195342A (https=)
WO (1) WO2007135179A1 (https=)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006117369A1 (de) * 2005-05-03 2006-11-09 Solvias Ag Ferrocenylliganden, herstellung und verwendung
US8415488B2 (en) 2007-11-20 2013-04-09 Solvias Ag Bidentate secondary phosphine oxide chiral ligands for use in asymmetric addition reactions
EP2186817A1 (en) * 2008-11-14 2010-05-19 Solvias AG Chiral ligands
CN112824422B (zh) * 2019-11-21 2023-01-13 中国科学院大连化学物理研究所 一种手性二茂铁-吲哚双膦配体及其制备方法和其应用
CN112480179B (zh) * 2020-11-24 2025-11-14 苏州鹏旭医药科技有限公司 一种取代二茂铁基二膦均相催化剂配体

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002527413A (ja) * 1998-10-13 2002-08-27 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 触媒用の重合体に担持された燐配位子
WO2004099226A1 (en) 2003-05-09 2004-11-18 Umicore Ag & Co. Kg Substituted ferrocenyldiphosphines as ligands for homogeneous hydrogenation catalysts
WO2005056568A1 (de) 2003-12-12 2005-06-23 Solvias Ag Ferrocenyl-1, 2-diphosphine, deren herstellung und deren verwendung
GB0400720D0 (en) 2004-01-14 2004-02-18 Stylacats Ltd Novel ferrocene-based phosphorus chiral phosphines
ES2293596T3 (es) * 2004-07-05 2008-03-16 Solvias Ag 1,1'-difosfinoferrocenos con restos quirales o aquirales enlazados en la posicion 2,2'.

Also Published As

Publication number Publication date
ES2493634T3 (es) 2014-09-12
US20090171114A1 (en) 2009-07-02
WO2007135179A1 (en) 2007-11-29
IL195342A (en) 2015-08-31
EP2027134A1 (en) 2009-02-25
EP2027134B1 (en) 2014-07-16
CN101448845A (zh) 2009-06-03
CA2653150A1 (en) 2007-11-29
IL195342A0 (en) 2009-08-03
US8008529B2 (en) 2011-08-30
JP2009537607A (ja) 2009-10-29
JP5209611B2 (ja) 2013-06-12
CN101448845B (zh) 2012-12-12

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