Title:
SYNTHESIS METHOD FOR BORONIC ACID ESTER COMPOUND, AND SODIUM SALT OF BORONIC ACID ESTER COMPOUND AND SYNTHESIS METHOD THEREFOR
Document Type and Number:
WIPO Patent Application WO/2019/142854
Kind Code:
A1
Abstract:
The present invention establishes a technique enabling easy synthesis of a boronic acid ester compound at low cost with high efficiency through a small number of steps without the need of a complicated chemical technique or reagents that need to be carefully handled. Also, established are a sodium salt of a boronic acid ester compound which is a novel compound, and a technique for synthesizing the sodium salt. This method for synthesizing a boronic acid ester compound or a sodium salt thereof, comprises a step for reacting, in an reaction solvent, an organic chloride with a dispersion in which sodium is dispersed in a dispersion solvent, to obtain an organic sodium compound, and for reacting the obtained organic sodium compound with a boric acid ester compound to obtain a boronic acid ester compound or a sodium salt of the boronic acid ester compound. Also provided is a sodium salt of the boronic acid ester compound.
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Inventors:
MURAKAMI YOSHIAKI (JP)
FUKUSHIMA MIYUKI (JP)
TAKAI KAZUHIKO (JP)
ASAKO SOBI (JP)
FUKUSHIMA MIYUKI (JP)
TAKAI KAZUHIKO (JP)
ASAKO SOBI (JP)
Application Number:
PCT/JP2019/001235
Publication Date:
July 25, 2019
Filing Date:
January 17, 2019
Export Citation:
Assignee:
KOBELCO ECO SOLUTIONS CO LTD (JP)
NAT UNIV CORPORATION OKAYAMA UNIV (JP)
NAT UNIV CORPORATION OKAYAMA UNIV (JP)
International Classes:
C07F5/04; C07F5/02
Domestic Patent References:
| WO2008093637A1 | 2008-08-07 | |||
| WO2013080583A1 | 2013-06-06 | |||
| WO2019004371A1 | 2019-01-03 |
Foreign References:
| JP2009102678A | 2009-05-14 | |||
| JP2006223345A | 2006-08-31 |
Other References:
LIQIONG WANG, MARK E. WELKER: "Preparation and Diels–Alder/Cross Coupling Reactions of New 2-Boron-Substituted 1,3-Dienes", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 77, no. 18, 2012, pages 8280 - 8286, XP055628576
LI; GAO-QIANG; ET AL: "Direct Conversion of Pinacol Arylboronic Esters to Aryl Triolborates", CHEMISTRY LETTERS, vol. 40, no. 7, 2011, pages 702 - 704, XP003031946, ISSN: 0366-7022
YAMAMOTO, YASUNORI; TAKIZAWA, MIHO; YU, XIAO-QIANG; MIYAURA, NORIO: "Palladium-Catalyzed Cross-Coupling Reaction of Heteroaryltriolborates with Aryl Halides for Synthesis of Biaryls", HETEROCYCLES, vol. 80, no. 1, 1 January 2010 (2010-01-01), pages 359 - 368, XP055718809, ISSN: 0385-5414, DOI: 10.3987/COM-09-S(S)30
ANDREW N CAMMIDGE ET AL: "Aryl Trihydroxyborates: Easily Isolated Discrete Species Convenient for Direct Application in Coupling Reactions", ORGANIC LETTERS, vol. 8, no. 18, 2006, pages 4071 - 4074, XP055164131, DOI: 10.1021/ol061564w
YASUNORI YAMAMOTO ET AL: "Cyclic Triolborates: Air- and Water-Stable Ate Complexes of Organoboronic Acids", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 47, no. 5, 2008, pages 928 - 931, XP055072727
MIYAURA N; SUZUKI A: "Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds", CHEMICAL REVIEWS, vol. 95, 1995, pages 2457 - 2483, XP002435837
YOSHIAKI MURAKAMI , MIYUKI FUKUSHIMA: "Development of new applications of SD (Sodium Dispersion)", KOBELCO ECO-SOLUTIONS ENGINEERING REPORTS, vol. 14, no. 1, 30 September 2017 (2017-09-30), pages 26 - 31, XP055718808
NAKAJIMA ET AL: "Preparation of aryl sodium compounds from aryl chlorides using sodium dispersion and its application to cross-coupling reaction", PROCEEDINGS OF THE CHEMICAL SOCIETY OF JAPAN, 98TH , vol. 98, 6 March 2018 (2018-03-06), pages H2-02, XP009522030
MIYAURA, N. ET AL., CHEM. REV., vol. 95, 1995, pages 2457 - 2483
YAMAMOTO, T. ET AL., ORGANIC LETTERS, vol. 13, no. 21, 2011, pages 5766 - 5769
HARRISSON, P. ET AL., SYNLETT, vol. 1, 2009, pages 147 - 150
MKHALID, I. A. I. ET AL., CHEM. REV., vol. 110, 2010, pages 890 - 931
See also references of EP 3741764A4
LI; GAO-QIANG; ET AL: "Direct Conversion of Pinacol Arylboronic Esters to Aryl Triolborates", CHEMISTRY LETTERS, vol. 40, no. 7, 2011, pages 702 - 704, XP003031946, ISSN: 0366-7022
YAMAMOTO, YASUNORI; TAKIZAWA, MIHO; YU, XIAO-QIANG; MIYAURA, NORIO: "Palladium-Catalyzed Cross-Coupling Reaction of Heteroaryltriolborates with Aryl Halides for Synthesis of Biaryls", HETEROCYCLES, vol. 80, no. 1, 1 January 2010 (2010-01-01), pages 359 - 368, XP055718809, ISSN: 0385-5414, DOI: 10.3987/COM-09-S(S)30
ANDREW N CAMMIDGE ET AL: "Aryl Trihydroxyborates: Easily Isolated Discrete Species Convenient for Direct Application in Coupling Reactions", ORGANIC LETTERS, vol. 8, no. 18, 2006, pages 4071 - 4074, XP055164131, DOI: 10.1021/ol061564w
YASUNORI YAMAMOTO ET AL: "Cyclic Triolborates: Air- and Water-Stable Ate Complexes of Organoboronic Acids", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 47, no. 5, 2008, pages 928 - 931, XP055072727
MIYAURA N; SUZUKI A: "Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds", CHEMICAL REVIEWS, vol. 95, 1995, pages 2457 - 2483, XP002435837
YOSHIAKI MURAKAMI , MIYUKI FUKUSHIMA: "Development of new applications of SD (Sodium Dispersion)", KOBELCO ECO-SOLUTIONS ENGINEERING REPORTS, vol. 14, no. 1, 30 September 2017 (2017-09-30), pages 26 - 31, XP055718808
NAKAJIMA ET AL: "Preparation of aryl sodium compounds from aryl chlorides using sodium dispersion and its application to cross-coupling reaction", PROCEEDINGS OF THE CHEMICAL SOCIETY OF JAPAN, 98TH , vol. 98, 6 March 2018 (2018-03-06), pages H2-02, XP009522030
MIYAURA, N. ET AL., CHEM. REV., vol. 95, 1995, pages 2457 - 2483
YAMAMOTO, T. ET AL., ORGANIC LETTERS, vol. 13, no. 21, 2011, pages 5766 - 5769
HARRISSON, P. ET AL., SYNLETT, vol. 1, 2009, pages 147 - 150
MKHALID, I. A. I. ET AL., CHEM. REV., vol. 110, 2010, pages 890 - 931
See also references of EP 3741764A4
Attorney, Agent or Firm:
R&C IP LAW FIRM (JP)
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