Title:
METHOD FOR PRODUCING MONO-CROSS-COUPLED AROMATIC COMPOUND HAVING LEAVING GROUP
Document Type and Number:
WIPO Patent Application WO/2021/177290
Kind Code:
A1
Abstract:
A method for producing a mono-cross-coupled aromatic compound (3-1), said method comprising: preparation of an aromatic compound (1) that has at least two leaving groups; preparation of a compound (2) that is capable of undergoing a cross-coupling reaction, while being selected from among aromatic boronic acids (2-1), aromatic amino compounds (2-2), diboronic acid esters (2-3), aromatic compounds (2-4) that have a hydroxyl group, and aromatic compounds (2-5) that have a thiol group; and a cross-coupling reaction of the aromatic compound (1) that has at least two leaving groups and the compound (2) in the presence of a palladium catalyst and a base and in the absence of a solvent.
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Inventors:
ITO HAJIME (JP)
KUBOTA KOJI (JP)
KUBOTA KOJI (JP)
Application Number:
PCT/JP2021/007912
Publication Date:
September 10, 2021
Filing Date:
March 02, 2021
Export Citation:
Assignee:
UNIV HOKKAIDO NAT UNIV CORP (JP)
International Classes:
C07C1/32; C07B61/00; C07C15/20; C07C17/26; C07C25/22; C07C41/30; C07C43/205; C07C209/68; C07C211/45; C07D333/16; C07D333/18; C07D333/56
Domestic Patent References:
| WO2020085396A1 | 2020-04-30 |
Foreign References:
| JP2020035093A | 2020-03-05 |
Other References:
KUBOTA KOJI, SEO TAMAE, KOIDE KATSUMASA, HASEGAWA YASUCHIKA, ITO HAJIME: "Olefin-accelerated solid-state C-N cross-coupling reactions using mechanochemistry", NATURE COMMUNICATIONS, vol. 10, no. 111, 2019, pages 1 - 11, XP055852814
S CHNEIDER, FRANZISKA ET AL.: "The Suzuki-Miyaura Reaction under Mechanochemical Conditions", ORGANIC PROCESS RESEARCH & DEVELOPMENT, vol. 13, no. 1, 2009, pages 44 - 48, XP055710687, DOI: 10.1021/op800148y
JIANC, ZHIJIANG ET AL.: "Liquid-Assisted Grinding Accelerating: Suzuki-Miyaura Reaction of Aryl Chlorides under High-Speed Ball-Milling Conditions", JOURNAL OF ORGANIC CHEMISTRY, vol. 81, no. 20, 2016, pages 10049 - 10055, XP055802690
STOLLE, ACHIM ET AL.: "Solvent-free reactions of alkynes in ball mills: it is definitely more than mixing", PURE AND APPLIED CHEMISTRY, vol. 83, no. 7, 2011, pages 1343 - 1349, XP055710703, DOI: 10.1351/PAC-CON-10-09-26
HERNANDEZ, J. G. ET AL.: "Useful chemical activation alternatives in solvent-free organic reactions", COMPREHENSIVE ORGANIC SYNTHESIS, vol. 9, 2014, pages 287 - 314, XP009527403
SEO TAMAE, KUBOTA KOJI, ITO HAJIME: "Selective mechanochemical monoarylation of unbiased dibromoarenes by in situ crystallization", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 142, no. 22, 27 April 2020 (2020-04-27), pages 9884 - 9889, XP055852821, DOI: 10.1021/jacs.0c01739
SEWAN THEERAMUNKONGANTONIO CALDARELLIALBERTO MASSAROTTISILVIO APRILEDIEGO CAPRIOGLIOROBERTA ZANINETTIALESSIA TERUGGITRACEY PIRALIG, J. MED. CHEM., vol. 54, 2011, pages 4977 - 4986
KOJI KUBOTATAMAE SEOKATSUMASA KOIDEYASUCHIKA HASEGAWAHAJIME ITO, NATURE COMMUNICATIONS, vol. 10, 2019, pages 111
SAKASHITA: "Powder Mixing Process Technology", COLORING MATERIAL, vol. 77, no. 2, 2004, pages 75 - 85
S CHNEIDER, FRANZISKA ET AL.: "The Suzuki-Miyaura Reaction under Mechanochemical Conditions", ORGANIC PROCESS RESEARCH & DEVELOPMENT, vol. 13, no. 1, 2009, pages 44 - 48, XP055710687, DOI: 10.1021/op800148y
JIANC, ZHIJIANG ET AL.: "Liquid-Assisted Grinding Accelerating: Suzuki-Miyaura Reaction of Aryl Chlorides under High-Speed Ball-Milling Conditions", JOURNAL OF ORGANIC CHEMISTRY, vol. 81, no. 20, 2016, pages 10049 - 10055, XP055802690
STOLLE, ACHIM ET AL.: "Solvent-free reactions of alkynes in ball mills: it is definitely more than mixing", PURE AND APPLIED CHEMISTRY, vol. 83, no. 7, 2011, pages 1343 - 1349, XP055710703, DOI: 10.1351/PAC-CON-10-09-26
HERNANDEZ, J. G. ET AL.: "Useful chemical activation alternatives in solvent-free organic reactions", COMPREHENSIVE ORGANIC SYNTHESIS, vol. 9, 2014, pages 287 - 314, XP009527403
SEO TAMAE, KUBOTA KOJI, ITO HAJIME: "Selective mechanochemical monoarylation of unbiased dibromoarenes by in situ crystallization", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 142, no. 22, 27 April 2020 (2020-04-27), pages 9884 - 9889, XP055852821, DOI: 10.1021/jacs.0c01739
SEWAN THEERAMUNKONGANTONIO CALDARELLIALBERTO MASSAROTTISILVIO APRILEDIEGO CAPRIOGLIOROBERTA ZANINETTIALESSIA TERUGGITRACEY PIRALIG, J. MED. CHEM., vol. 54, 2011, pages 4977 - 4986
KOJI KUBOTATAMAE SEOKATSUMASA KOIDEYASUCHIKA HASEGAWAHAJIME ITO, NATURE COMMUNICATIONS, vol. 10, 2019, pages 111
SAKASHITA: "Powder Mixing Process Technology", COLORING MATERIAL, vol. 77, no. 2, 2004, pages 75 - 85
Attorney, Agent or Firm:
YAMAO, Norihito et al. (JP)
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