Title:
REACTION METHOD AND DEVICE USED IN REACTION THEREIN
Document Type and Number:
WIPO Patent Application WO/2022/092260
Kind Code:
A1
Abstract:
The present invention addresses the problem of providing a cross-coupling reaction method that can use a wide variety of compounds as starting materials, that can substantially not use organic solvent, and that can rapidly provide reaction products at high yields using a simple and convenient means. The present invention also addresses the problem of providing novel compounds that have not heretofore been obtainable. The following reaction method is provided as the solution: the reaction, by a mechanochemical procedure, of a leaving group-bearing organic compound (A) having a melting point of at least 30°C and an organic compound (B) that has a melting point of at least 30°C and is reactive with the leaving group-bearing organic compound, by the application of mechanical energy to the organic compound (A) and the organic compound (B) in the presence of a catalyst under conditions of a temperature of 60-500°C and an amount of organic solvent present of not more than 0.7 mL per 1 mmol of the total of the organic compound (A) and the organic compound (B).
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Inventors:
ITO HAJIME (JP)
KUBOTA KOJI (JP)
KUBOTA KOJI (JP)
Application Number:
PCT/JP2021/040001
Publication Date:
May 05, 2022
Filing Date:
October 29, 2021
Export Citation:
Assignee:
UNIV HOKKAIDO NAT UNIV CORP (JP)
International Classes:
C07C1/32; C07C15/14; C07C15/24; C07C17/26; C07C25/22; C07C41/30; C07C43/205; C07C43/215; C07C45/68; C07C49/665; C07C49/84; C07C209/68; C07C211/45; C07C211/54; C07C221/00; C07C225/22; C07C231/12; C07C233/07; C07D209/34; C07D209/86; C07D213/16; C07D263/56; C07D285/14; C07D333/04; C07D333/64; C07D471/04; C07D495/14; C07D498/22; C07F5/02; C07F7/08; C07B61/00
Domestic Patent References:
| WO2008142635A2 | 2008-11-27 | |||
| WO2020085396A1 | 2020-04-30 | |||
| WO2020009016A1 | 2020-01-09 | |||
| WO2021177290A1 | 2021-09-10 |
Foreign References:
| JPH07325329A | 1995-12-12 |
Other References:
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CAS REGISTRY NO. 2011721-19-8. DATABASE REGISTRY. [online]. 13 October 2016, [retrieval date 02 December 2021], Retrieved from: STN entire text
SALZNER ULRIKE: "Effects of Perfluorination on Thiophene and Pyrrole Oligomers", THE JOURNAL OF PHYSICAL CHEMISTRY A, vol. 114, no. 16, 29 April 2010 (2010-04-29), US , pages 5397 - 5405, XP055926519, ISSN: 1089-5639, DOI: 10.1021/jp1005633
XU, Z. ; FICHOU, D. ; HOROWITZ, G. ; GARNIER, F.: "Electrochemical synthesis of alpha-conjugated octi- and decithienyl oligomers", JOURNAL OF ELECTROANALYTICAL CHEMISTRY AND INTERFACIAL ELECTROCHEMISTRY, vol. 267, no. 1-2, 10 August 1989 (1989-08-10), NL , pages 339 - 342, XP026532915, ISSN: 0022-0728, DOI: 10.1016/0022-0728(89)80266-9
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FOMINE SERGUEI, GUADARRAMA PATRICIA, FLORES PAOLA: "Oligothiophene Catenanes and Knots. Part II. Mono and Dications. A Theoretical Study", THE JOURNAL OF PHYSICAL CHEMISTRY A, vol. 111, no. 16, 1 April 2007 (2007-04-01), US , pages 3124 - 3131, XP055926523, ISSN: 1089-5639, DOI: 10.1021/jp0677750
ALKAN FAHRI, SALZNER ULRIKE: "Theoretical Investigation of Excited States of Oligothiophene Anions", THE JOURNAL OF PHYSICAL CHEMISTRY A, vol. 112, no. 27, 1 July 2008 (2008-07-01), US , pages 6053 - 6058, XP055926524, ISSN: 1089-5639, DOI: 10.1021/jp711135e
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, 1 December 2019 (2019-12-01), pages 1 - 11, XP055852814, DOI: 10.1038/s41467-018-08017-9
SEO TAMAE, ISHIYAMA TATSUO, KUBOTA KOJI, ITO HAJIME: "Solid-state Suzuki–Miyaura cross-coupling reactions: olefin-accelerated C–C coupling using mechanochemistry", CHEMICAL SCIENCE, vol. 10, no. 35, 1 January 2019 (2019-01-01), United Kingdom , pages 8202 - 8210, XP055926527, ISSN: 2041-6520, DOI: 10.1039/C9SC02185J
JIANG ZHI-JIANG, LI ZHEN-HUA, YU JING-BO, SU WEI-KE: "Liquid-Assisted Grinding Accelerating: Suzuki–Miyaura Reaction of Aryl Chlorides under High-Speed Ball-Milling Conditions", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 81, no. 20, 21 October 2016 (2016-10-21), pages 10049 - 10055, XP055802690, ISSN: 0022-3263, DOI: 10.1021/acs.joc.6b01938
FRANZISKA SCHNEIDER, ACHIM STOLLE, BERND ONDRUSCHKA, HENNING HOPF: "The Suzuki−Miyaura Reaction under Mechanochemical Conditions §", ORGANIC PROCESS RESEARCH & DEVELOPMENT, vol. 13, no. 1, 16 January 2009 (2009-01-16), US , pages 44 - 48, XP055710687, ISSN: 1083-6160, DOI: 10.1021/op800148y
CAS REGISTRY NO. 2011721-19-8. DATABASE REGISTRY. [online]. 13 October 2016, [retrieval date 02 December 2021], Retrieved from: STN entire text
SALZNER ULRIKE: "Effects of Perfluorination on Thiophene and Pyrrole Oligomers", THE JOURNAL OF PHYSICAL CHEMISTRY A, vol. 114, no. 16, 29 April 2010 (2010-04-29), US , pages 5397 - 5405, XP055926519, ISSN: 1089-5639, DOI: 10.1021/jp1005633
XU, Z. ; FICHOU, D. ; HOROWITZ, G. ; GARNIER, F.: "Electrochemical synthesis of alpha-conjugated octi- and decithienyl oligomers", JOURNAL OF ELECTROANALYTICAL CHEMISTRY AND INTERFACIAL ELECTROCHEMISTRY, vol. 267, no. 1-2, 10 August 1989 (1989-08-10), NL , pages 339 - 342, XP026532915, ISSN: 0022-0728, DOI: 10.1016/0022-0728(89)80266-9
BELJONNE D., CORNIL J., FRIEND R. H., JANSSEN R. A. J., BRÉDAS J. L.: "Influence of Chain Length and Derivatization on the Lowest Singlet and Triplet States and Intersystem Crossing in Oligothiophenes", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 118, no. 27, 1 January 1996 (1996-01-01), pages 6453 - 6461, XP055926522, ISSN: 0002-7863, DOI: 10.1021/ja9531135
FOMINE SERGUEI, GUADARRAMA PATRICIA, FLORES PAOLA: "Oligothiophene Catenanes and Knots. Part II. Mono and Dications. A Theoretical Study", THE JOURNAL OF PHYSICAL CHEMISTRY A, vol. 111, no. 16, 1 April 2007 (2007-04-01), US , pages 3124 - 3131, XP055926523, ISSN: 1089-5639, DOI: 10.1021/jp0677750
ALKAN FAHRI, SALZNER ULRIKE: "Theoretical Investigation of Excited States of Oligothiophene Anions", THE JOURNAL OF PHYSICAL CHEMISTRY A, vol. 112, no. 27, 1 July 2008 (2008-07-01), US , pages 6053 - 6058, XP055926524, ISSN: 1089-5639, DOI: 10.1021/jp711135e
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, 1 December 2019 (2019-12-01), pages 1 - 11, XP055852814, DOI: 10.1038/s41467-018-08017-9
SEO TAMAE, ISHIYAMA TATSUO, KUBOTA KOJI, ITO HAJIME: "Solid-state Suzuki–Miyaura cross-coupling reactions: olefin-accelerated C–C coupling using mechanochemistry", CHEMICAL SCIENCE, vol. 10, no. 35, 1 January 2019 (2019-01-01), United Kingdom , pages 8202 - 8210, XP055926527, ISSN: 2041-6520, DOI: 10.1039/C9SC02185J
JIANG ZHI-JIANG, LI ZHEN-HUA, YU JING-BO, SU WEI-KE: "Liquid-Assisted Grinding Accelerating: Suzuki–Miyaura Reaction of Aryl Chlorides under High-Speed Ball-Milling Conditions", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 81, no. 20, 21 October 2016 (2016-10-21), pages 10049 - 10055, XP055802690, ISSN: 0022-3263, DOI: 10.1021/acs.joc.6b01938
FRANZISKA SCHNEIDER, ACHIM STOLLE, BERND ONDRUSCHKA, HENNING HOPF: "The Suzuki−Miyaura Reaction under Mechanochemical Conditions §", ORGANIC PROCESS RESEARCH & DEVELOPMENT, vol. 13, no. 1, 16 January 2009 (2009-01-16), US , pages 44 - 48, XP055710687, ISSN: 1083-6160, DOI: 10.1021/op800148y
Attorney, Agent or Firm:
YAMADA, Yasuyuki et al. (JP)
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