WO2009008447A1 - 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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WO2009008447A1
WO2009008447A1 PCT/JP2008/062401 JP2008062401W WO2009008447A1 WO 2009008447 A1 WO2009008447 A1 WO 2009008447A1 JP 2008062401 W JP2008062401 W JP 2008062401W WO 2009008447 A1 WO2009008447 A1 WO 2009008447A1
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group
branched
linear
catalyst composition
compound
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PCT/JP2008/062401
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English (en)
French (fr)
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Masaharu Nakamura
Takuji Hatakeyama
Hisao Eguchi
Hirokazu Yano
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Kyoto University
Tosoh Corporation
Tosoh Finechem Corporation
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Priority to KR1020107002715A priority Critical patent/KR101494149B1/ko
Priority to CN2008801066687A priority patent/CN101835535B/zh
Priority to EP08790988.3A priority patent/EP2168680A4/en
Priority to US12/668,338 priority patent/US20100185019A1/en
Publication of WO2009008447A1 publication Critical patent/WO2009008447A1/ja

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    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2265—Carbenes or carbynes, i.e.(image)
    • B01J31/2269—Heterocyclic carbenes
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    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
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    • 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
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    • 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
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    • 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
    • B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
    • B01J31/28—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of the platinum group metals, iron group metals or copper
    • B01J31/30—Halides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B37/00—Reactions without formation or introduction of functional groups containing hetero atoms, involving either the formation of a carbon-to-carbon bond between two carbon atoms not directly linked already or the disconnection of two directly linked carbon atoms
    • C07B37/04—Substitution
    • 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
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    • 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
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
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    • C07—ORGANIC CHEMISTRY
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    • C07C43/00—Ethers; Compounds having groups, groups or groups
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
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    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
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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
    • B01J2231/4233—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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    • B01J2231/40—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
    • B01J2231/4238—Negishi-type, i.e. RY + R'ZnZ, in which R, R' is optionally substituted alkyl, alkenyl, alkynyl, aryl, Y is the leaving group and Z is halide or R'
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    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
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    • C07C2527/128—Compounds comprising a halogen and an iron group metal or a platinum group metal
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    • C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • C07C2531/24—Phosphines

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

　ニッケル金属源、フッ素源、および、特定構造の含窒素複素環化合物またはホスフィン化合物を含有するクロスカップリング反応用触媒組成物。該触媒組成物の存在下で、式（２）：　Ｒ5－ＭＹ1　または式（３）：　Ｒ5－Ｍ－Ｒ5（式中、Ｒ5はアリール基、ヘテロアリール基、直線状、分岐状または環状のアルキル基、または直線状、分岐状または環状のアルケニル基を示す。ＭはＭｇ原子またはＺｎ原子を示し、Ｙ1はハロゲン基を示す。）で表される有機金属化合物と、 式（４）：Ｒ6－Ｙ2（式中、Ｒ6はアリール基、ヘテロアリール基、直線状、分岐状または環状のアルキル基、または直線状、分岐状または環状のアルケニル基を示す。Ｙ2はハロゲン原子、メタンスルホナート基、トルエンスルホナート基またはトリフルオロメタンスルホナート基を示す。）で表される化合物とを反応させると、クロスカップリング化合物　Ｒ5－Ｒ6　が高い選択率で得られる。
PCT/JP2008/062401 2007-07-11 2008-07-09 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 WO2009008447A1 (ja)

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KR1020107002715A KR101494149B1 (ko) 2007-07-11 2008-07-09 촉매 조성물 및 이것을 이용한 크로스커플링 화합물의 제조방법
CN2008801066687A CN101835535B (zh) 2007-07-11 2008-07-09 催化剂组合物及使用该催化剂组合物的交叉偶联化合物的制造方法
EP08790988.3A EP2168680A4 (en) 2007-07-11 2008-07-09 A CATALYST COMPOSITION AND METHOD FOR PRODUCING A CROSS-LINKING COMPOUND THEREWITH
US12/668,338 US20100185019A1 (en) 2007-07-11 2008-07-09 Catalyst composition and process for producing cross-coupled compound using same

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JP2007181653 2007-07-11
JP2007-181653 2007-07-11

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US (1) US20100185019A1 (ja)
EP (1) EP2168680A4 (ja)
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Cited By (1)

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Publication number Priority date Publication date Assignee Title
JP2014024777A (ja) * 2012-07-25 2014-02-06 Asahi Kasei Corp ハロゲン原子を有する多環式芳香族化合物の製造方法

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JP5614985B2 (ja) * 2007-03-09 2014-10-29 国立大学法人京都大学 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
GB2497346A (en) * 2011-12-09 2013-06-12 Merck Patent Gmbh Preparation of biaryl or aryl-heteroaryl compounds using biarylzinc derivatives
CN103288583B (zh) * 2013-06-14 2016-03-23 中国科学院长春应用化学研究所 一种2,3,3’,4’-四甲基联苯的制备方法
CN106316745A (zh) * 2016-08-24 2017-01-11 苏州氟拓化工科技有限公司 一种联苯化合物的制备方法
CN108456172B (zh) * 2018-04-20 2021-01-12 浙江大学城市学院 一种具有苯并咪唑骨架的手性氮杂环卡宾前体化合物及其制备方法和应用
EP3971222A4 (en) * 2019-11-27 2024-02-21 Maruzen Petrochemical Co., Ltd. COMPLEX CONNECTION AND PRODUCTION PROCESS THEREOF
CN115093440B (zh) * 2022-08-29 2022-12-06 南昌大学 一种氢硅烷化合物与氮杂环芳烃化合物交叉偶联的方法

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014024777A (ja) * 2012-07-25 2014-02-06 Asahi Kasei Corp ハロゲン原子を有する多環式芳香族化合物の製造方法

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KR101494149B1 (ko) 2015-02-17
CN101835535B (zh) 2012-11-07
CN101835535A (zh) 2010-09-15
JP5156510B2 (ja) 2013-03-06
EP2168680A4 (en) 2013-09-04
US20100185019A1 (en) 2010-07-22
KR20100031764A (ko) 2010-03-24
EP2168680A1 (en) 2010-03-31
JP2009034672A (ja) 2009-02-19

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