WO2008111414A1 - 触媒組成物及びそれを用いたクロスカップリング化合物の製造方法 - Google Patents

触媒組成物及びそれを用いたクロスカップリング化合物の製造方法 Download PDF

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Publication number
WO2008111414A1
WO2008111414A1 PCT/JP2008/053751 JP2008053751W WO2008111414A1 WO 2008111414 A1 WO2008111414 A1 WO 2008111414A1 JP 2008053751 W JP2008053751 W JP 2008053751W WO 2008111414 A1 WO2008111414 A1 WO 2008111414A1
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Prior art keywords
catalyst composition
cross
production
same
coupling compound
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PCT/JP2008/053751
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English (en)
French (fr)
Inventor
Masaharu Nakamura
Takuji Hatakeyama
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Kyoto University
Tosoh Finechem Corporation
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Application filed by Kyoto University, Tosoh Finechem Corporation filed Critical Kyoto University
Priority to JP2009503968A priority Critical patent/JP5614985B2/ja
Priority to US12/529,297 priority patent/US8211820B2/en
Publication of WO2008111414A1 publication Critical patent/WO2008111414A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/32—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen
    • C07C1/325—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a metal atom
    • C07C1/326—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a metal atom the hetero-atom being a magnesium atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
    • C07C17/2632—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions involving an organo-magnesium compound, e.g. Grignard synthesis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
    • 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
    • C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—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
    • 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
    • C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C07D233/58—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
    • 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
    • B01J2531/84—Metals of the iron group
    • B01J2531/842—Iron
    • 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
    • B01J2531/84—Metals of the iron group
    • B01J2531/845—Cobalt
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • C07C2531/22—Organic complexes

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  • 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)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

本発明は、鉄又はコバルトのフッ化物及び一般式（１Ａ）又は（１Ｂ）［式中、Ｒ１及びＲ２は、同一又は異なっていてもよく、置換もしくは無置換のアリール基等を示す。Ｒ３及びＲ４は、同一又は異なっていてもよく、水素等を示す。（Ⅰ）は、単結合又は二重結合を示す。Ｘ－は、一価の陰イオンを示す。］で示される含窒素複素環化合物を含む触媒組成物ならびに当該触媒組成物の存在下で、有機ハロゲン化合物（３）と有機マグネシウム化合物（２）とを反応させる、クロスカップリング化合物を製造するための方法を提供する。
PCT/JP2008/053751 2007-03-09 2008-03-03 触媒組成物及びそれを用いたクロスカップリング化合物の製造方法 WO2008111414A1 (ja)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2009503968A JP5614985B2 (ja) 2007-03-09 2008-03-03 触媒組成物及びそれを用いたクロスカップリング化合物の製造方法
US12/529,297 US8211820B2 (en) 2007-03-09 2008-03-03 Catalyst composition, and process for production of cross-coupling compound using the same

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2007-060926 2007-03-09
JP2007060926 2007-03-09

Publications (1)

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WO2008111414A1 true WO2008111414A1 (ja) 2008-09-18

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PCT/JP2008/053751 WO2008111414A1 (ja) 2007-03-09 2008-03-03 触媒組成物及びそれを用いたクロスカップリング化合物の製造方法

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US (1) US8211820B2 (ja)
JP (1) JP5614985B2 (ja)
WO (1) WO2008111414A1 (ja)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014134773A (ja) * 2012-12-14 2014-07-24 Canon Inc 電子写真感光体、プロセスカートリッジおよび電子写真装置、ならびに、フタロシアニン結晶

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000229243A (ja) * 1999-02-09 2000-08-22 Tosoh Corp クロスカップリング反応用触媒、並びにそれを用いた置換スチレン誘導体又は置換ビアリール誘導体の製造方法
JP2003212798A (ja) * 2001-11-19 2003-07-30 Sumitomo Chem Co Ltd 置換芳香族化合物類の製造方法
JP2004091465A (ja) * 2001-10-23 2004-03-25 Sumitomo Chem Co Ltd カップリング化合物の製造方法
WO2005075384A1 (ja) * 2004-02-10 2005-08-18 Japan Science And Technology Agency 芳香族化合物の製造方法
JP2005534711A (ja) * 2002-08-07 2005-11-17 ユミコア・アクチエンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフト 新規ニッケル−、パラジウム−及び白金−カルベン錯体、それらの製造及び触媒反応における使用
JP2006151947A (ja) * 2004-11-02 2006-06-15 Yokohama National Univ 末端オレフィンの二量化反応による線状化合物の製法

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JP2827050B2 (ja) 1990-11-06 1998-11-18 北興化学工業株式会社 ４―ｔｅｒｔ―ブトキシ―４′―フルオロビフェニルおよびその製造法
DE19836470A1 (de) 1998-08-12 2000-02-17 Clariant Gmbh Verfahren zur Herstellung von 4-Chlorbiphenylen
US7041856B2 (en) * 2001-10-23 2006-05-09 Sumitomo Chemical Company, Limited Coupling catalyst and process using the same
US7122711B2 (en) * 2001-11-19 2006-10-17 Sumitomo Chemical Company, Limited Method for producing biaryl compound
JP4576584B2 (ja) 2005-01-31 2010-11-10 独立行政法人科学技術振興機構 リン含有高分子固定化パラジウム触媒およびその使用
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Patent Citations (6)

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JP2000229243A (ja) * 1999-02-09 2000-08-22 Tosoh Corp クロスカップリング反応用触媒、並びにそれを用いた置換スチレン誘導体又は置換ビアリール誘導体の製造方法
JP2004091465A (ja) * 2001-10-23 2004-03-25 Sumitomo Chem Co Ltd カップリング化合物の製造方法
JP2003212798A (ja) * 2001-11-19 2003-07-30 Sumitomo Chem Co Ltd 置換芳香族化合物類の製造方法
JP2005534711A (ja) * 2002-08-07 2005-11-17 ユミコア・アクチエンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフト 新規ニッケル−、パラジウム−及び白金−カルベン錯体、それらの製造及び触媒反応における使用
WO2005075384A1 (ja) * 2004-02-10 2005-08-18 Japan Science And Technology Agency 芳香族化合物の製造方法
JP2006151947A (ja) * 2004-11-02 2006-06-15 Yokohama National Univ 末端オレフィンの二量化反応による線状化合物の製法

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HATAKEYAMA T. ET AL.: "Iron-Catalyzed Selective Biaryl Coupling: Remarkable Suppression of Homocoupling by the Fluoride Anion", J. AM. CHEM. SOC., vol. 129, no. 32, 15 August 2007 (2007-08-15), pages 9844 - 9845 *

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JPWO2008111414A1 (ja) 2010-06-24
US8211820B2 (en) 2012-07-03
JP5614985B2 (ja) 2014-10-29
US20100094018A1 (en) 2010-04-15

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