WO2024142966A1 - 高分子メカノラジカル開始剤及び高分子メカノラジカル開始剤を用いる反応方法 - Google Patents

高分子メカノラジカル開始剤及び高分子メカノラジカル開始剤を用いる反応方法 Download PDF

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WO2024142966A1
WO2024142966A1 PCT/JP2023/044838 JP2023044838W WO2024142966A1 WO 2024142966 A1 WO2024142966 A1 WO 2024142966A1 JP 2023044838 W JP2023044838 W JP 2023044838W WO 2024142966 A1 WO2024142966 A1 WO 2024142966A1
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French (fr)
Japanese (ja)
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肇 伊藤
浩司 久保田
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Hokkaido University NUC
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B31/00—Reduction in general
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B61/00—Other general methods
    • 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
    • C07C1/26—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only halogen atoms as hetero-atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
    • C07C17/12—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the ring of aromatic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
    • C07C17/14—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the side-chain of aromatic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/23—Preparation of halogenated hydrocarbons by dehalogenation
    • 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
    • C07C209/74—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 by halogenation, hydrohalogenation, dehalogenation, or dehydrohalogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
    • 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
    • C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen atoms
    • 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
    • C07C41/24—Preparation of ethers by reactions not forming ether-oxygen bonds by elimination of halogens, e.g. elimination of HCl
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
    • C07C2601/20—Systems containing only non-condensed rings with a ring being at least seven-membered the ring being twelve-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/56—Ring systems containing bridged rings
    • C07C2603/58—Ring systems containing bridged rings containing three rings
    • C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
    • C07C2603/74—Adamantanes

Definitions

  • One of the problems that the present invention aims to solve is to provide a polymeric mechano-radical initiator obtained by mechanochemically treating an organic polymer material as a radical initiator for a reaction in which the polymeric mechano-radical initiator components are not incorporated into the reaction product.
  • One of the problems that the present invention aims to solve is to provide a reaction method for radically reducing an organic halogen compound, which uses a polymeric mechano-radical initiator obtained by mechanochemically treating an organic polymer material as a radical initiator.
  • a reaction method for C—H fluorination of a substrate using a polymeric mechano-radical initiator comprising: The method includes a step of mechanochemically treating at least an organic polymer material, a substrate, and a fluorination reagent in a reaction vessel, The substrate comprises a compound having a C—H bond based on a secondary or tertiary carbon; The reaction method.
  • a polymeric mechano-radical initiator obtained by mechanochemically treating an organic polymeric material is provided as a radical initiator for a reaction in which the polymeric mechano-radical initiator component is not incorporated into the reaction product.
  • the present invention provides a reaction method for radically reducing an organic halogen compound, which uses, as a radical initiator, a polymeric mechano-radical initiator obtained by mechanochemically treating an organic polymer material.
  • the present invention provides a reaction method for radically cyclizing an organic halogen compound, which uses, as a radical initiator, a polymeric mechano-radical initiator obtained by mechanochemically treating an organic polymer material.
  • the present invention provides a reaction method for C-H fluorination of a compound having a C-H bond based on a secondary carbon or a tertiary carbon, which uses a polymeric mechano-radical initiator obtained by mechanochemical treatment of an organic polymer material.
  • a first aspect of the present invention is a polymeric mechano-radical initiator obtained by mechanochemical treatment of an organic polymer material, the polymeric mechano-radical initiator being used in a reaction in which no polymeric mechano-radical initiator components are incorporated into the reaction product.
  • a second aspect of the present invention is a reaction method for radically reducing and/or radically cyclizing a substrate using a polymeric mechano-radical initiator, the reaction method comprising a step of mechanochemically treating at least an organic polymer material and a substrate in a reaction vessel, the substrate comprising an organic halogen compound.
  • a third aspect of the present invention is a reaction method for C—H fluorination of a substrate using a polymeric mechano-radical initiator, the reaction method including at least a step of mechanochemically treating an organic polymer material, a substrate, and a fluorination reagent in a reaction vessel, the substrate including a compound having a C—H bond based on a secondary carbon or a tertiary carbon.
  • the organic polymeric material to be mechanochemically treated is not particularly limited.
  • one or more selected from the group consisting of polymeric materials obtained by addition polymerization of compounds having carbon-carbon unsaturated bonds such as vinyl monomers, and polymeric materials obtained by condensation polymerization reactions can be used.
  • the details of the "organic polymer material” and the “mechanochemical treatment” are the same as those in the above-mentioned [organic polymer material] and [mechanochemical treatment], and the details of the "polymeric mechano-radical initiator” are the same as those in the above-mentioned [polymeric mechano-radical initiator].
  • the details of the “organic polymer material” and the “mechanochemical treatment” are the same as those in the above [Organic polymer material] and [Mechanochemical treatment], and the details of the “polymeric mechano-radical initiator” are the same as those in the above [Polymeric mechano-radical initiator].
  • the fluorination reagent in the reaction method for C-H fluorination (C-H radical fluorination) of a substrate using the polymeric mechano radical initiator of the invention according to the fourth aspect is not particularly limited as long as it is a fluorination reagent capable of fluorinating a C-H bond based on a secondary carbon or a tertiary carbon.
  • a fluorination reagent capable of fluorinating a C-H bond based on a secondary carbon or a tertiary carbon can be used.
  • an electrophilic fluorinating agent can be used.
  • a commercially available product may be used as the fluorination reagent.
  • the GC yield of the reaction product was 10%.
  • Example 8 In a 5 mL stainless steel ball mill jar containing a 10 mm diameter stainless steel ball, 44.2 mg (0.2 mmol) of 1-Bromodecane (A-1) as a substrate, 119.3 mg (0.48 mmol (2.4 equiv. relative to the substrate)) of Tris(trimethylsilyl)silane as a reducing agent, and 300 mg of ultra-high molecular weight polyethylene (Aldrich "434272-100G”) (B-1) as an organic polymer material were added under air.
  • A-1Bromodecane A-1
  • Tris(trimethylsilyl)silane Tris(trimethylsilyl)silane
  • B-1 ultra-high molecular weight polyethylene
  • Example 28 to 35 The reaction products (C-1), (C-2), (C-4), and (C-5) shown in Table 3 were obtained in the same manner as in Example 27, except that the compounds (A-2) to (A-6) and (A-9) to (A-11) shown in Table 3 were used as substrates.
  • the GC yields of each reaction product are also shown in Table 3.
  • Example 38 In a 5 mL stainless steel ball mill jar containing a 10 mm diameter stainless steel ball, 52.0 mg (0.20 mmol) of 1-Bromo-2-(allyloxy)benzene (G-1) was added as a substrate, 119.3 mg (0.48 mmol; 2.4 equiv. relative to the substrate) of Tris(trimethylsilyl)silane as a reducing agent, and 300 mg of ultra-high molecular weight polyethylene (Aldrich "434272-100G”) (B-1) as an organic polymer material were added under air.
  • G-1 1-Bromo-2-(allyloxy)benzene
  • Example 39 and 40> The reaction products (H-2) to (H-3) shown in Table 4 were obtained in the same manner as in Example 38, except that the compounds (G-2) to (G-3) shown in Table 4 were used as substrates.
  • the isolated yield, NMR yield, or GC yield of each reaction product is also shown in Table 4.
  • the reaction was carried out by shaking and stirring at a vibration frequency of 30 Hz for 60 minutes while heating the ball mill jar from the outside (internal temperature 60°C) with a heat gun set at 100°C. After the reaction was completed, the mixture was dissolved in ethyl acetate, filtered, and then the ethyl acetate was removed with an evaporator. The crude product was purified by silica gel column chromatography to obtain 1-Fluoroadamantane as the reaction product. The NMR yield of the reaction product was 17%.
  • the lid of the ball mill jar was closed, the ball mill jar was attached to a ball mill, and the reaction was carried out by shaking and stirring at a vibration frequency of 25 Hz for 60 minutes while heating the ball mill jar from the outside (internal temperature 80°C) with a heat gun set to 160°C.
  • the mixture was dissolved in ethyl acetate, filtered, and the ethyl acetate was removed with an evaporator.
  • the crude product was purified by silica gel column chromatography to obtain Adamantane (C-2) as a reaction product.
  • the isolated yield of the reaction product was 85%.
  • Example 43 In a 5 mL stainless steel ball mill jar containing a stainless steel ball with a diameter of 10 mm, 32.1 mg (0.05 mmol) of 1,2,5,6,9,10-Hexabromocyclodecane as a substrate, 124.3 mg (0.5 mmol; 10 equiv. to the substrate) of Tris(trimethylsilyl)silane as a reducing agent, and 300 mg of ultra-high molecular weight polyethylene (434272-100G manufactured by Aldrich) as an organic polymer material were added under air.
  • the ball mill jar was attached to a ball mill, and the reaction was carried out by shaking and stirring at a vibration frequency of 30 Hz for 60 minutes while heating the ball mill jar from the outside (internal temperature 60°C) with a heat gun set to 100°C.
  • the mixture was dissolved in ethyl acetate, filtered, and the ethyl acetate was removed with an evaporator.
  • the crude product was purified by silica gel column chromatography to obtain naphthalene as a reaction product.
  • the GC yield of the reaction product was 69%.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
PCT/JP2023/044838 2022-12-28 2023-12-14 高分子メカノラジカル開始剤及び高分子メカノラジカル開始剤を用いる反応方法 Ceased WO2024142966A1 (ja)

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JP2024567468A JPWO2024142966A1 (https=) 2022-12-28 2023-12-14
EP23911747.6A EP4644354A4 (en) 2022-12-28 2023-12-14 POLYMER MECHANODAL INITIATOR AND REACTION PROCESS USING A POLYMER MECHANODAL INITIATOR

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Citations (7)

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WO2003095523A1 (fr) * 2002-05-08 2003-11-20 Japan Science And Technology Corporation Polymere decomposable a la chaleur
JP2012088358A (ja) 2010-10-15 2012-05-10 Konica Minolta Opto Inc 光学フィルム、偏光板、及び液晶表示装置
WO2020009016A1 (ja) * 2018-07-05 2020-01-09 ユニチカ株式会社 有機化合物の製造方法
WO2020085396A1 (ja) * 2018-10-23 2020-04-30 国立大学法人北海道大学 溶媒を使用しないクロスカップリング反応及びその反応を用いる製造方法
JP2021173603A (ja) 2020-04-23 2021-11-01 国立大学法人東京工業大学 メカノラジカル検出又は測定方法
WO2022092260A1 (ja) * 2020-10-30 2022-05-05 国立大学法人北海道大学 反応方法及びその反応に用いる装置
WO2023167321A1 (ja) * 2022-03-04 2023-09-07 国立大学法人北海道大学 メカノケミカル反応用添加剤、メカノケミカル方法、配位子化合物及び錯体

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003095523A1 (fr) * 2002-05-08 2003-11-20 Japan Science And Technology Corporation Polymere decomposable a la chaleur
JP2012088358A (ja) 2010-10-15 2012-05-10 Konica Minolta Opto Inc 光学フィルム、偏光板、及び液晶表示装置
WO2020009016A1 (ja) * 2018-07-05 2020-01-09 ユニチカ株式会社 有機化合物の製造方法
WO2020085396A1 (ja) * 2018-10-23 2020-04-30 国立大学法人北海道大学 溶媒を使用しないクロスカップリング反応及びその反応を用いる製造方法
JP2021173603A (ja) 2020-04-23 2021-11-01 国立大学法人東京工業大学 メカノラジカル検出又は測定方法
WO2022092260A1 (ja) * 2020-10-30 2022-05-05 国立大学法人北海道大学 反応方法及びその反応に用いる装置
WO2023167321A1 (ja) * 2022-03-04 2023-09-07 国立大学法人北海道大学 メカノケミカル反応用添加剤、メカノケミカル方法、配位子化合物及び錯体

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EP4644354A1 (en) 2025-11-05
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