WO2003043735A3 - P-funktionalisierte amine n-haltiger aromaten, deren herstellung und ihre verwendung in katalytischen reaktionen - Google Patents

P-funktionalisierte amine n-haltiger aromaten, deren herstellung und ihre verwendung in katalytischen reaktionen Download PDF

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Publication number
WO2003043735A3
WO2003043735A3 PCT/EP2002/013048 EP0213048W WO03043735A3 WO 2003043735 A3 WO2003043735 A3 WO 2003043735A3 EP 0213048 W EP0213048 W EP 0213048W WO 03043735 A3 WO03043735 A3 WO 03043735A3
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Prior art keywords
radical
aromatic
production
nitrogen atom
catalytic reactions
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PCT/EP2002/013048
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English (en)
French (fr)
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WO2003043735A2 (de
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Rhett Kempe
Thomas Schareina
Axel Monsees
Thomas Riermeier
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Evonik Operations GmbH
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Degussa GmbH
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Priority to EP02803396A priority Critical patent/EP1446224B1/de
Priority to AU2002366231A priority patent/AU2002366231A1/en
Priority to DE50205724T priority patent/DE50205724D1/de
Priority to JP2003545407A priority patent/JP2005509666A/ja
Priority to US10/495,969 priority patent/US20060058178A1/en
Publication of WO2003043735A2 publication Critical patent/WO2003043735A2/de
Publication of WO2003043735A3 publication Critical patent/WO2003043735A3/de
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D241/20—Nitrogen atoms
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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    • 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
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
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    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07F9/650952—Six-membered rings having the nitrogen atoms in the positions 1 and 4
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    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
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    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
    • B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
    • B01J2231/4211—Suzuki-type, i.e. RY + R'B(OR)2, in which R, R' are optionally substituted alkyl, alkenyl, aryl, acyl and Y is the leaving group
    • B01J2231/4227—Suzuki-type, i.e. RY + R'B(OR)2, in which R, R' are optionally substituted alkyl, alkenyl, aryl, acyl and Y is the leaving group with Y= Cl
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    • B01J2231/4233—Kumada-type, i.e. RY + R'MgZ, in which Ris optionally substituted alkyl, alkenyl, aryl, Y is the leaving group and Z is halide
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    • B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
    • B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
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    • B01J2231/4266—Sonogashira-type, i.e. RY + HC-CR' triple bonds, in which R=aryl, alkenyl, alkyl and R'=H, alkyl or aryl
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    • 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
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    • 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
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    • B01J31/1845—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 phosphorus
    • B01J31/1875—Phosphinites (R2P(OR), their isomeric phosphine oxides (R3P=O) and RO-substitution derivatives thereof)
    • B01J31/188—Amide derivatives thereof

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Catalysts (AREA)
  • Fats And Perfumes (AREA)

Abstract

Die Erfindung betrifft neue Liganden der Formel (I): R1(R2)P-N(R')R', worin R1 und R2 für einen beliebigen Rest, bevorzugt für einen Phenyl-, Cyclohexyl oder tert. Butyl-Rest stehen, und worin R' für einen stickstoffhaltigen hereocyclischen Aromaten steht, der mindestens 1 N-Atom enthält, wobei der Aromat in 2-Stellung zum aromatischen Stickstoffatom an das Stickstoffatom gemäss Formel (I) gebunden ist, und worin R' für Trimethylsilyl oder einen aromatischen Rest steht, ihre Herstellung und ihre Verwendung in Gegenwart von Übergangsmetallverbindungen der VIII. Nebengruppe des Periodensystems der Elemente für katalytische Reaktionen, besonders zur Veredelung von Halogenaromaten zur Produktion von Arylolefinen, Dienen, Diarylen, Bensoesäure- und Acrylsäurederivaten, Arylalkanen und Aminen.
PCT/EP2002/013048 2001-11-23 2002-11-21 P-funktionalisierte amine n-haltiger aromaten, deren herstellung und ihre verwendung in katalytischen reaktionen Ceased WO2003043735A2 (de)

Priority Applications (5)

Application Number Priority Date Filing Date Title
EP02803396A EP1446224B1 (de) 2001-11-23 2002-11-21 P-funktionalisierte amine n-haltiger aromaten, deren herstellung und ihre verwendung in katalytischen reaktionen
AU2002366231A AU2002366231A1 (en) 2001-11-23 2002-11-21 Aromatic compounds containing nitrogen and p-functionalized amines, the production thereof and their use in catalytic reactions
DE50205724T DE50205724D1 (de) 2001-11-23 2002-11-21 P-funktionalisierte amine n-haltiger aromaten, deren herstellung und ihre verwendung in katalytischen reaktionen
JP2003545407A JP2005509666A (ja) 2001-11-23 2002-11-21 Ｎ−含有芳香族化合物のｐ−官能化されたアミン、その製造及び触媒反応におけるその使用
US10/495,969 US20060058178A1 (en) 2001-11-23 2002-11-21 Aromatic compounds containing nitrogen and p- functionalized amines, the production thereof and their use in catalytic reactions

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10157358.8 2001-11-23
DE10157358A DE10157358A1 (de) 2001-11-23 2001-11-23 P-funktionalisierte Amine N-haltiger Aromaten, deren Herstellung und ihre Verwendung in katalytischen Reaktionen

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WO2003043735A2 WO2003043735A2 (de) 2003-05-30
WO2003043735A3 true WO2003043735A3 (de) 2004-03-04

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US (1) US20060058178A1 (de)
EP (1) EP1446224B1 (de)
JP (1) JP2005509666A (de)
AT (1) ATE316421T1 (de)
AU (1) AU2002366231A1 (de)
DE (2) DE10157358A1 (de)
WO (1) WO2003043735A2 (de)

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US7521581B2 (en) * 2005-03-30 2009-04-21 Tosoh Corporation Catalyst composition and process for producing cross-coupled compound using same
US9546191B1 (en) 2016-03-25 2017-01-17 King Fahd University Of Petroleum And Minerals Palladium(II) complex for catalyzing sonogashira coupling reactions and a method thereof
CN109776617B (zh) * 2019-01-23 2021-04-27 昆明贵金属研究所 一种丙酮配位双核钯化合物及其制备方法和应用

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EP1132361A1 (de) * 2000-03-06 2001-09-12 Solvias AG Organische Verbindungen durch Kopplung von Nukleophilen, Vinylverbindungen oder CO mit Wasser, Alkohole oder Aminen

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EP0124154A2 (de) * 1983-04-22 1984-11-07 Shell Internationale Researchmaatschappij B.V. Anilin-Verbindungen, ihre Herstellung, diese enthaltende Zusammensetzungen und Verfahren zur Bekämpfung von Pilzwachstum und/oder zur Bekämpfung oder Regulierung von Pflanzenwachstum
US5977361A (en) * 1997-10-16 1999-11-02 Yale University Transition metal-catalyzed process for preparing N-aryl compounds
EP1132361A1 (de) * 2000-03-06 2001-09-12 Solvias AG Organische Verbindungen durch Kopplung von Nukleophilen, Vinylverbindungen oder CO mit Wasser, Alkohole oder Aminen

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AU2002366231A8 (en) 2003-06-10
JP2005509666A (ja) 2005-04-14
AU2002366231A1 (en) 2003-06-10
DE50205724D1 (de) 2006-04-13
EP1446224A2 (de) 2004-08-18
ATE316421T1 (de) 2006-02-15
DE10157358A1 (de) 2003-08-07

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