Title:
METHOD FOR PRODUCING AROMATIC COMPOUND
Document Type and Number:
WIPO Patent Application WO/2023/243522
Kind Code:
A1
Abstract:
The purpose of the present invention is to provide a method for producing an aromatic compound, wherein a cross-coupling reaction by means of a mechanochemical process is carried out in a state where a solvent is not substantially contained, the method being able to be applied to a wide range of base materials. A method for producing an aromatic compound according to the present invention performs a cross-coupling reaction of an aromatic compound (A) that has a leaving group and a compound (B) that can be cross-coupled in the presence of a palladium catalyst (C) and a base (D) in a state where a solvent is not substantially contained. This method for producing an aromatic compound comprises: a step in which a solution of the palladium catalyst (C) is prepared; and a step in which a cross-coupling reaction is carried out by adding and mixing the solution of the palladium catalyst (C) to and with a mixture that contains the aromatic compound (A) that has a leaving group, the compound (B) that can be cross-coupled, and the base (D).
Inventors:
SAWATSUGAWA YUKI (JP)
TAMURA KEN (JP)
ITO HAJIME (JP)
KUBOTA KOJI (JP)
TAMURA KEN (JP)
ITO HAJIME (JP)
KUBOTA KOJI (JP)
Application Number:
PCT/JP2023/021260
Publication Date:
December 21, 2023
Filing Date:
June 07, 2023
Export Citation:
Assignee:
NIPPON CHEMICAL IND (JP)
UNIV HOKKAIDO NAT UNIV CORP (JP)
UNIV HOKKAIDO NAT UNIV CORP (JP)
International Classes:
C07C17/269; C07B61/00; C07C22/08; C07C25/18; C07C41/30; C07C43/20; C07C43/205; C07C253/30; C07C255/50; C07D295/096
Domestic Patent References:
| WO2022092260A1 | 2022-05-05 | |||
| WO2020085396A1 | 2020-04-30 |
Foreign References:
| JP2003019436A | 2003-01-21 |
Other References:
KUBOTA, KOJI; ITO, HAJIME: "Development of Selective Reactions Using Ball Milling", YUKI GOSEI KAGAKU KYOKAISHI - JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY, YUKI GOSEI KAGAKU KYOKAI, JP, vol. 79, no. 5, 1 May 2021 (2021-05-01), JP , pages 118 (492) - 128 (502), XP009551531, ISSN: 0037-9980, DOI: 10.5059/yukigoseikyokaishi.79.492
TAKAHASHI RIKURO, SEO TAMAE, KUBOTA KOJI, ITO HAJIME: "Palladium-Catalyzed Solid-State Polyfluoroarylation of Aryl Halides Using Mechanochemistry", ACS CATALYSIS, AMERICAN CHEMICAL SOCIETY, US, vol. 11, no. 24, 17 December 2021 (2021-12-17), US , pages 14803 - 14810, XP093117504, ISSN: 2155-5435, DOI: 10.1021/acscatal.1c03731
SEO TAMAE, TOYOSHIMA NAOKI, KUBOTA KOJI, ITO HAJIME: "Tackling Solubility Issues in Organic Synthesis: Solid-State Cross-Coupling of Insoluble Aryl Halides", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 143, no. 16, 28 April 2021 (2021-04-28), pages 6165 - 6175, XP093117506, ISSN: 0002-7863, DOI: 10.1021/jacs.1c00906
SAULI VUOTI; JUHO AUTIO; MINNA LAITILA; MATTI HAUKKA; JOUNI PURSIAINEN: "Palladium‐Catalyzed Suzuki–Miyaura Cross‐Coupling of Various Aryl Halides Using ortho‐Alkyl‐Substituted Arylphosphanes and (ortho‐Alkylphenyl)alkylphosphanes under Microwave Heating", EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, WILEY-VCH VERLAG , WENHEIM, DE, vol. 2008, no. 3, 20 November 2007 (2007-11-20), DE , pages 397 - 407, XP072117213, ISSN: 1434-1948, DOI: 10.1002/ejic.200700705
TAKAHASHI RIKURO, SEO TAMAE, KUBOTA KOJI, ITO HAJIME: "Palladium-Catalyzed Solid-State Polyfluoroarylation of Aryl Halides Using Mechanochemistry", ACS CATALYSIS, AMERICAN CHEMICAL SOCIETY, US, vol. 11, no. 24, 17 December 2021 (2021-12-17), US , pages 14803 - 14810, XP093117504, ISSN: 2155-5435, DOI: 10.1021/acscatal.1c03731
SEO TAMAE, TOYOSHIMA NAOKI, KUBOTA KOJI, ITO HAJIME: "Tackling Solubility Issues in Organic Synthesis: Solid-State Cross-Coupling of Insoluble Aryl Halides", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 143, no. 16, 28 April 2021 (2021-04-28), pages 6165 - 6175, XP093117506, ISSN: 0002-7863, DOI: 10.1021/jacs.1c00906
SAULI VUOTI; JUHO AUTIO; MINNA LAITILA; MATTI HAUKKA; JOUNI PURSIAINEN: "Palladium‐Catalyzed Suzuki–Miyaura Cross‐Coupling of Various Aryl Halides Using ortho‐Alkyl‐Substituted Arylphosphanes and (ortho‐Alkylphenyl)alkylphosphanes under Microwave Heating", EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, WILEY-VCH VERLAG , WENHEIM, DE, vol. 2008, no. 3, 20 November 2007 (2007-11-20), DE , pages 397 - 407, XP072117213, ISSN: 1434-1948, DOI: 10.1002/ejic.200700705
Attorney, Agent or Firm:
SHOWA INTERNATIONAL PATENT FIRM (JP)
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