Title:
METHOD FOR PRODUCING ORGANIC METAL NUCLEOPHILIC AGENT AND REACTION METHOD USING ORGANIC METAL NUCLEOPHILIC AGENT
Document Type and Number:
WIPO Patent Application WO/2022/196796
Kind Code:
A1
Abstract:
The first problem addressed by the present invention is to provide a simple method for producing an organic metal nucleophilic agent, the method being reduced in environmental load by reducing the amount of an organic solvent used therein, without requiring large-scale equipment by making it unnecessary to regulate the atmosphere or the water content (moisture content); the second problem addressed by the present invention is to provide a reaction method which is advantageous from the aspect of cost since a reaction between an organic metal nucleophilic agent and various organic electrophiles is able to be carried out by a simple and efficient means such as a one-pot process; and the third problem addressed by the present invention is to provide a simple method for producing an organic metal nucleophilic agent that has more excellent reactivity. As a solution, the present invention provides a method for producing an organic metal nucleophilic agent, wherein an organic halide and a metal or metal compound are reacted with each other by a mechanochemical process in the presence of 0.5 to 10.0 equivalent weights of an ether compound per 1 equivalent weight of the organic halide.
Inventors:
ITO HAJIME (JP)
KUBOTA KOJI (JP)
KUBOTA KOJI (JP)
Application Number:
PCT/JP2022/012524
Publication Date:
September 22, 2022
Filing Date:
March 18, 2022
Export Citation:
Assignee:
UNIV HOKKAIDO NAT UNIV CORP (JP)
International Classes:
C07B49/00; C07C29/40; C07C33/20; C07C33/24; C07C33/34; C07C33/50; C07C45/00; C07C45/61; C07C49/11; C07F3/02
Foreign References:
| JPH05112501A | 1993-05-07 | |||
| JP2016525504A | 2016-08-25 | |||
| US20190161505A1 | 2019-05-30 | |||
| JP2008174472A | 2008-07-31 | |||
| JPS5773010A | 1982-05-07 | |||
| JPH0433985B2 | 1992-06-04 | |||
| JP2002030003A | 2002-01-29 |
Other References:
UMENO MASAYUKI, HAMADA MITSUO: "Applications of the Grignard Reaction", YUKI GOSEI KAGAKU KYOKAISHI - JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY, vol. 38, no. 12, 1 December 1988 (1988-12-01), JP , pages 1196 - 1209, XP055967310, ISSN: 0037-9980, DOI: 10.5059/yukigoseikyokaishi.38.1196
DANIEL C. WADDELL; TAMMARA D. CLARK; JAMES MACK: "Conducting moisture sensitive reactions under mechanochemical conditions", TETRAHEDRON LETTERS, vol. 53, no. 34, 22 August 2012 (2012-08-22), Amsterdam , NL , pages 4510 - 4513, XP028432658, ISSN: 0040-4039, DOI: 10.1016/j.tetlet.2012.06.009
RINA TAKAHASHI, ANQI HU, YADONG PANG, TAMAE SEO, KOJI KUBOTA , HAJIME ITO: "Solvent-less mechanochemical synthesis of magnesium-based carbon nucleophiles and their application to organic synthesis", THE 101ST CSJ ANNUAL MEETING, no. A15-4am-05, 4 March 2010 (2010-03-04), pages 1 - 1, XP055969162
TAKAHASHI RINA, HU ANQI, GAO PAN, GAO YUNPENG, PANG YADONG, SEO TAMAE, JIANG JULONG, MAEDA SATOSHI, TAKAYA HIKARU, KUBOTA KOJI, IT: "Mechanochemical synthesis of magnesium-based carbon nucleophiles in air and their use in organic synthesis", NATURE COMMUNICATIONS, vol. 12, no. 1, 1 December 2021 (2021-12-01), pages 1 - 10, XP055969163, DOI: 10.1038/s41467-021-26962-w
FRESENIUS ENCIRONMENTAL BULLETIN, vol. 20
AUSTRALIAN JOURNAL OF CHEMISTRY, vol. 54
MOLECULES, vol. 25, 2020, pages 570
DANIEL C. WADDELL; TAMMARA D. CLARK; JAMES MACK: "Conducting moisture sensitive reactions under mechanochemical conditions", TETRAHEDRON LETTERS, vol. 53, no. 34, 22 August 2012 (2012-08-22), Amsterdam , NL , pages 4510 - 4513, XP028432658, ISSN: 0040-4039, DOI: 10.1016/j.tetlet.2012.06.009
RINA TAKAHASHI, ANQI HU, YADONG PANG, TAMAE SEO, KOJI KUBOTA , HAJIME ITO: "Solvent-less mechanochemical synthesis of magnesium-based carbon nucleophiles and their application to organic synthesis", THE 101ST CSJ ANNUAL MEETING, no. A15-4am-05, 4 March 2010 (2010-03-04), pages 1 - 1, XP055969162
TAKAHASHI RINA, HU ANQI, GAO PAN, GAO YUNPENG, PANG YADONG, SEO TAMAE, JIANG JULONG, MAEDA SATOSHI, TAKAYA HIKARU, KUBOTA KOJI, IT: "Mechanochemical synthesis of magnesium-based carbon nucleophiles in air and their use in organic synthesis", NATURE COMMUNICATIONS, vol. 12, no. 1, 1 December 2021 (2021-12-01), pages 1 - 10, XP055969163, DOI: 10.1038/s41467-021-26962-w
FRESENIUS ENCIRONMENTAL BULLETIN, vol. 20
AUSTRALIAN JOURNAL OF CHEMISTRY, vol. 54
MOLECULES, vol. 25, 2020, pages 570
Attorney, Agent or Firm:
YAMADA, Yasuyuki et al. (JP)
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