Title:
METHOD FOR PRODUCING FLUORINATED ORGANIC COMPOUND
Document Type and Number:
WIPO Patent Application WO/2024/029525
Kind Code:
A1
Abstract:
Provided is a novel method for producing a fluorinated organic compound. The production method is a method for producing a fluorine adduct of a compound represented by formula (1) (in the formula, R1, R2, and n have the same meanings as the symbols described in the specification.), said method including a step that reacts the compound represented by formula (1) with (A) at least one fluorine source selected from hydrogen fluoride, hydrogen fluoride salts, and fluoride salts, (B) at least one iodine source selected from iodine, iodoaliphatic compounds, and iodoaromatic ring compounds, and (C) at least one compound selected from compounds represented by formula (2-1) (in the formula, X represents a conjugate base of a Bronsted acid.) and multimers thereof, optionally having one or more substituents, to add fluorine to the double bond or triple bond.
Inventors:
HIGASHI MASAHIRO (JP)
KISHIKAWA YOSUKE (JP)
KITAMURA TSUGIO (JP)
OYAMADA JUZO (JP)
KISHIKAWA YOSUKE (JP)
KITAMURA TSUGIO (JP)
OYAMADA JUZO (JP)
Application Number:
PCT/JP2023/028100
Publication Date:
February 08, 2024
Filing Date:
August 01, 2023
Export Citation:
Assignee:
DAIKIN IND LTD (JP)
UNIV SAGA (JP)
UNIV SAGA (JP)
International Classes:
C07C17/02; B01J31/02; C07C19/08; C07C22/04; C07C25/02; C07C29/62; C07C31/38; C07C45/63; C07C49/80; C07C49/813; C07C67/307; C07C69/65; C07D213/89
Domestic Patent References:
| WO2019189862A1 | 2019-10-03 | |||
| WO2022131378A1 | 2022-06-23 |
Foreign References:
| JP2000103748A | 2000-04-11 |
Other References:
MOLNÁR ISTVÁN GÁBOR, GILMOUR RYAN: "Catalytic Difluorination of Olefins", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 138, no. 15, 20 April 2016 (2016-04-20), pages 5004 - 5007, XP093136698, ISSN: 0002-7863, DOI: 10.1021/jacs.6b01183
CHENGFENG YE, BRENDAN TWAMLEY, JEAN'NE M. SHREEVE: "Straightforward Syntheses of Hypervalent Iodine(III) Reagents Mediated by Selectfluor", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, vol. 7, no. 18, 1 September 2005 (2005-09-01), pages 3961 - 3964, XP055178585, ISSN: 15237060, DOI: 10.1021/ol051446t
UMEMOTO T., ET AL.: "POWER AND STRUCTURE-VARIABLE FLUORINATING AGENTS. ÖTHE N-FLUOROPYRIDINIUM SALT SYSTEM.", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 112, no. 23, 7 November 1990 (1990-11-07), pages 8563 - 8575, XP000564081, ISSN: 0002-7863, DOI: 10.1021/ja00179a047
KITAMURA, TSUGIO: "Iodoarene-Catalyzed Fluorination Reactions Using 1,1’-Difluoro-2,2’- bipyridinium Bis(tetrafluoroborate) as a Terminal Oxidant", PROCEEDINGS OF THE 49TH SYMPOSIUM ON MAIN GROUP ELEMENT CHEMISTRY, 2 December 2022 (2022-12-02), pages 72
KITAMURA TSUGIO, KITAMURA DAICHI, OYAMADA JUZO, HIGASHI MASAHIRO, KISHIKAWA YOSUKE: "N , N’ ‐Difluoro‐2,2’‐bipyridinium Bis(tetrafluoroborate): a New Terminal Oxidant for Iodoarene‐catalyzed Fluorination Reactions", ADVANCED SYNTHESIS AND CATALYSIS, JOHN WILEY & SONS, INC., HOBOKEN, USA, vol. 365, no. 16, 15 August 2023 (2023-08-15), Hoboken, USA, pages 2744 - 2750, XP093136703, ISSN: 1615-4150, DOI: 10.1002/adsc.202300265
CHENGFENG YE, BRENDAN TWAMLEY, JEAN'NE M. SHREEVE: "Straightforward Syntheses of Hypervalent Iodine(III) Reagents Mediated by Selectfluor", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, vol. 7, no. 18, 1 September 2005 (2005-09-01), pages 3961 - 3964, XP055178585, ISSN: 15237060, DOI: 10.1021/ol051446t
UMEMOTO T., ET AL.: "POWER AND STRUCTURE-VARIABLE FLUORINATING AGENTS. ÖTHE N-FLUOROPYRIDINIUM SALT SYSTEM.", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 112, no. 23, 7 November 1990 (1990-11-07), pages 8563 - 8575, XP000564081, ISSN: 0002-7863, DOI: 10.1021/ja00179a047
KITAMURA, TSUGIO: "Iodoarene-Catalyzed Fluorination Reactions Using 1,1’-Difluoro-2,2’- bipyridinium Bis(tetrafluoroborate) as a Terminal Oxidant", PROCEEDINGS OF THE 49TH SYMPOSIUM ON MAIN GROUP ELEMENT CHEMISTRY, 2 December 2022 (2022-12-02), pages 72
KITAMURA TSUGIO, KITAMURA DAICHI, OYAMADA JUZO, HIGASHI MASAHIRO, KISHIKAWA YOSUKE: "N , N’ ‐Difluoro‐2,2’‐bipyridinium Bis(tetrafluoroborate): a New Terminal Oxidant for Iodoarene‐catalyzed Fluorination Reactions", ADVANCED SYNTHESIS AND CATALYSIS, JOHN WILEY & SONS, INC., HOBOKEN, USA, vol. 365, no. 16, 15 August 2023 (2023-08-15), Hoboken, USA, pages 2744 - 2750, XP093136703, ISSN: 1615-4150, DOI: 10.1002/adsc.202300265
Attorney, Agent or Firm:
SAEGUSA & PARTNERS (JP)
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