Title:
METHOD FOR PRODUCING FLUORINATED COMPOUND
Document Type and Number:
WIPO Patent Application WO/2019/245008
Kind Code:
A1
Abstract:
The present invention addresses the problem of providing a new method for producing a compound including a fluoromethylene group. The problem is accomplished by a method for producing a compound represented by formula (1) (wherein R1 is an organic group, RA is a hydrogen atom or a fluorine atom, R4a is a hydrogen atom or an organic group, R4b is a hydrogen atom or an organic group, R5
a is a hydrogen atom or an organic group, R5b is a hydrogen atom or an organic group, and R2 is a hydrogen atom or an organic group, and wherein R2 may have been linked to R4a to form a ring), the method comprising step A in which a compound represented by formula (2) (wherein X1 is a leaving group and the other symbols are the same as defined above) is reacted with a compound represented by formula (3) (wherein X2 is a leaving group and the other symbols are the same as defined above) optionally in the presence of a reducing agent with light irradiation.
Inventors:
MATSUURA MAKOTO (JP)
KUROKI YOSHICHIKA (JP)
KISHIKAWA YOSUKE (JP)
RYU ILHYONG (JP)
FUKUYAMA TAKAHIDE (JP)
KUROKI YOSHICHIKA (JP)
KISHIKAWA YOSUKE (JP)
RYU ILHYONG (JP)
FUKUYAMA TAKAHIDE (JP)
Application Number:
PCT/JP2019/024610
Publication Date:
December 26, 2019
Filing Date:
June 20, 2019
Export Citation:
Assignee:
DAIKIN IND LTD (JP)
UNIV OSAKA PUBLIC CORP (JP)
UNIV OSAKA PUBLIC CORP (JP)
International Classes:
C07C17/26; B01J31/22; B01J35/02; C07C21/18; C07C22/08; C07C67/343; C07C69/65; C07C231/12; C07C233/09; C07B61/00
Domestic Patent References:
| WO2017154948A1 | 2017-09-14 | |||
| WO2017154948A1 | 2017-09-14 |
Other References:
KOSOBOKOV, MIKHAIL D. ET AL.: "Geminal Silicon/Zinc Reagent as an Equivalent of Difluoromethylene Bis-carbanion", ORGANIC LETTERS, vol. 16, no. 5, 19 February 2014 (2014-02-19), pages 1438 - 1441, XP055665798, ISSN: 1523-7060, DOI: 10.1021/ol5002297
SATO, K. ET AL.: "Reactions of ethyl bromodifluoroacetate in the presence of copper powder", JOURNAL OF FLUORINE CHEMISTRY, vol. 125, no. 4, 1 April 2004 (2004-04-01), pages 509 - 515, XP004507051, ISSN: 0022-1139, DOI: 10.1016/j.jfluchem.2003.11.023
SI , CHONG ET AL.: "An efficient synthesis of 3, 4- dihydropyridone via a tandem olefin isomerization- ring-closing metathesis reaction", TETRAHEDRON LETTERS, vol. 55, no. 40, 1 October 2014 (2014-10-01), pages 5529 - 5532, XP055665807, ISSN: 0040-4039, DOI: 10.1016/j.tetlet.2014.08.025
SUMINO, SHUHEI ET AL.: "Photoredox-catalyzed hydrodifluoroalkylation of alkenes using difluoroharoalkyl compounds and a Hantzsch ester", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 82, no. 10, 5 May 2017 (2017-05-05), pages 5469 - 5474, XP055665809, ISSN: 0022-3263, DOI: 10.1021/acs.joc.7b00609
SUMINO, SHUHEI ET AL.: "Palladium/Light induced radical alkenylation and allylation of alkyl iodides using alkenyl and allylic sulfones", ORGANIC LETTERS, vol. 20, no. 4, 6 February 2018 (2018-02-06), pages 1078 - 1081, XP055665815, ISSN: 1523-7060, DOI: 10.1021/acs.orglett.7b04050
HEITZ, DREW R. ET AL.: "Visible-Light-mediated alkenylation, allylation, and cyanation of pottasium alkenyl trifluoroborates with organic photoredox catalysts", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 81, no. 16, 23 June 2016 (2016-06-23), pages 7308 - 7313, XP055665818, ISSN: 0022-3263, DOI: 10.1021/acs.joc.6b01207
UNO, MISAE ET AL.: "Synthesis of 4,4- Difluoroalkenes by Coupling of a-Substituted a, alpha- Difluoromethyl Halides with Allyl Sulfones under Photoredox Catalyzed Conditions", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 84, no. 14, 2 July 2019 (2019-07-02), pages 9330 - 9338, XP055665820, ISSN: 0022-3263, DOI: 10.1021/acs.joc.9b00901
JOHN T. WELCH ET AL., TETRAHEDRON, vol. 43, no. 14, 1987, pages 3123
SVANTE ET AL., J. AM. CHEM. SOC., vol. 103, 1981, pages 4452
See also references of EP 3812359A4
SATO, K. ET AL.: "Reactions of ethyl bromodifluoroacetate in the presence of copper powder", JOURNAL OF FLUORINE CHEMISTRY, vol. 125, no. 4, 1 April 2004 (2004-04-01), pages 509 - 515, XP004507051, ISSN: 0022-1139, DOI: 10.1016/j.jfluchem.2003.11.023
SI , CHONG ET AL.: "An efficient synthesis of 3, 4- dihydropyridone via a tandem olefin isomerization- ring-closing metathesis reaction", TETRAHEDRON LETTERS, vol. 55, no. 40, 1 October 2014 (2014-10-01), pages 5529 - 5532, XP055665807, ISSN: 0040-4039, DOI: 10.1016/j.tetlet.2014.08.025
SUMINO, SHUHEI ET AL.: "Photoredox-catalyzed hydrodifluoroalkylation of alkenes using difluoroharoalkyl compounds and a Hantzsch ester", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 82, no. 10, 5 May 2017 (2017-05-05), pages 5469 - 5474, XP055665809, ISSN: 0022-3263, DOI: 10.1021/acs.joc.7b00609
SUMINO, SHUHEI ET AL.: "Palladium/Light induced radical alkenylation and allylation of alkyl iodides using alkenyl and allylic sulfones", ORGANIC LETTERS, vol. 20, no. 4, 6 February 2018 (2018-02-06), pages 1078 - 1081, XP055665815, ISSN: 1523-7060, DOI: 10.1021/acs.orglett.7b04050
HEITZ, DREW R. ET AL.: "Visible-Light-mediated alkenylation, allylation, and cyanation of pottasium alkenyl trifluoroborates with organic photoredox catalysts", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 81, no. 16, 23 June 2016 (2016-06-23), pages 7308 - 7313, XP055665818, ISSN: 0022-3263, DOI: 10.1021/acs.joc.6b01207
UNO, MISAE ET AL.: "Synthesis of 4,4- Difluoroalkenes by Coupling of a-Substituted a, alpha- Difluoromethyl Halides with Allyl Sulfones under Photoredox Catalyzed Conditions", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 84, no. 14, 2 July 2019 (2019-07-02), pages 9330 - 9338, XP055665820, ISSN: 0022-3263, DOI: 10.1021/acs.joc.9b00901
JOHN T. WELCH ET AL., TETRAHEDRON, vol. 43, no. 14, 1987, pages 3123
SVANTE ET AL., J. AM. CHEM. SOC., vol. 103, 1981, pages 4452
See also references of EP 3812359A4
Attorney, Agent or Firm:
SAEGUSA & PARTNERS (JP)
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