Title:
FLUORINE-CONTAINING COMPLEX COMPOUND, AND PRODUCTION METHOD FOR FLUORINE-CONTAINING ORGANIC COMPOUND EMPLOYING SAME
Document Type and Number:
WIPO Patent Application WO/2015/050236
Kind Code:
A1
Abstract:
The purpose of the present invention is to make possible synthesis of various fluorine-containing compounds having organic groups at both terminals of a tetrafluoroethylene structure (-CF2-CF2-). The present invention provides fluorine-containing complex compounds which include ligands selected from the group consisting of fluorine-containing-organic compounds represented by formula (1a): R1-CF2-CF2-M1 (1a) (wherein M1 represents a metal selected from the group consisting of copper, zinc, nickel, iron, cobalt, and tin; and R1 represents an organic group), compounds having the pyridine ring, and phosphines.
Inventors:
ADACHI KENJI
SHIBANUMA TAKASHI
NAGAI TAKABUMI
OGOSHI SENSUKE (JP)
OHASHI MASATO (JP)
SHIBANUMA TAKASHI
NAGAI TAKABUMI
OGOSHI SENSUKE (JP)
OHASHI MASATO (JP)
Application Number:
PCT/JP2014/076474
Publication Date:
April 09, 2015
Filing Date:
October 02, 2014
Export Citation:
Assignee:
DAIKIN IND LTD (JP)
UNIV OSAKA (JP)
UNIV OSAKA (JP)
International Classes:
C07F1/08; C07B37/04; C07C17/263; C07C22/08; C07C37/18; C07C39/367; C07C41/30; C07C43/225; C07C45/45; C07C47/55; C07C49/233; C07C49/235; C07C49/84; C07C67/333; C07C69/65; C07C69/76; C07C209/68; C07C211/52; C07C253/30; C07C255/50; C07C381/00; C07D213/26; C07D307/87; C07D333/12; C07F5/02; C07F7/12; C07F7/18
Domestic Patent References:
| WO2012024564A1 | 2012-02-23 |
Foreign References:
| JPS4712775A | ||||
| CA995250A | 1976-08-17 | |||
| JPH05331084A | 1993-12-14 | |||
| JPH04288344A | 1992-10-13 | |||
| US3297591A | 1967-01-10 | |||
| JP2004143280A | 2004-05-20 | |||
| JP2010224066A | 2010-10-07 |
Other References:
LITVINAS, NICHOLE D. ET AL.: "A General Strategy for the Perfluoroalkylation of Arenes and Arylbromides by Using Arylboronate Esters and [(phen)CuRF", ANGEWANDTE CHEMIE , INTERNATIONAL EDITION, vol. 51, no. 2, 2012, pages 536 - 539
MORIMOTO, HIROYUKI ET AL.: "A Broadly Applicable Copper Reagent for Trifluoromethylations and Perfluoroalkylations of Aryl Iodides and Bromides", ANGEWANDTE CHEMIE , INTERNATIONAL EDITION, vol. 50, no. 16, 2011, pages 3793 - 3798
FIELDS, ROY ET AL.: "Metal carbonyl chemistry. IX. Improved syntheses and some reactions of tetracarbonylcyclooctafluorotetramethyleneiron", JOURNAL OF THE CHEMICAL SOCIETY [SECTION] A: INORGANIC, PHYSICAL, THEORETICAL, 1970, pages 1964 - 9
BRUNNER, HENRI ET AL.: "Asymmetric catalysis. XXXVII. Complexes with free donor groups as co- catalysts for enantioselective hydrosilylation", JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol. 335, no. 1, 1987, pages 15 - 27
HUGHES, RUSSE LL P. ET AL.: "Fluoroalkylation of cobalt complexes: selective reactions at the metal or the cyclopentadienyl ring", JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol. 548, no. 1, 1997, pages 109 - 112
MARCHESE, A. L. ET AL.: "Perfluoroalkyl derivatives of chromium and cobalt containing sulfur donor ligands", JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol. 121, no. 1, 1976, pages 63 - 71
TREICHEL, P. M. ET AL.: "Ionic perfluoroalkyl complexes of cobalt", INORGANIC CHEMISTRY, vol. 4, no. 8, 1965, pages 1098 - 102
HU , CHANGMING ET AL.: "Cobaloxime-catalyzed hydroperfluoroalkylation of electron-deficient alkenes with perfluoroalkyl halides: reaction and mechanism", JOURNAL OF ORGANIC CHEMISTRY, vol. 57, no. 12, 1992, pages 3339 - 42
FUKUHARA, TADAHITO ET AL.: "Polyfluorination using IF5", JOURNAL OF ORGANIC CHEMISTRY, vol. 75, no. 21, 2010, pages 7393 - 7399
MOBBS, R. H.: "Heptafluorobenzyl bromide", JOURNAL OF FLUORINE CHEMISTRY, vol. 1, no. 3, 1972, pages 361 - 4
YAGUPOL'SKII, L. M. ET AL.: "Effect of substituents having a trifluoromethyl group on the reactivity of aromatic compounds", ZHURNAL OBSHCHEI KHIMII, vol. 34, no. 11, 1964, pages 3682 - 90
KNUNYANTS, I. L. ET AL.: "omega- Phenylperfluoroolefins and omega- phenylperfluorocarboxylic acids", IZVESTIYA AKADEMII NAUK SSSR, SERIYA KHIMICHESKAYA, 1967, pages 74 - 8
HIROKI SAIJO ET AL.: "Cu(I) o Mochiita TFE eno 1,2-Aryl Fuka Hanno ni yoru ArCF2CF2Ar' Goseiho no Kaihatsu", ABSTRACTS OF THE FLUORINE CONFERENCE OF JAPAN, vol. 36TH, 3 October 2013 (2013-10-03), pages 142 - 143
HIROKI SAIJO ET AL.: "Cu(I) o Mochiita Tetrafluoroethylene no 1,2-Diaryl Fuka Hanno", CSJ: THE CHEMICAL SOCIETY OF JAPAN DAI 94 SHUNKI NENKAI KOEN YOKOSHU IV, vol. 94TH, 12 March 2014 (2014-03-12), pages 1227 - 2 B1-06
MORIMOTO, HIROYUKI ET AL.: "A Broadly Applicable Copper Reagent for Trifluoromethylations and Perfluoroalkylations of Aryl Iodides and Bromides", ANGEWANDTE CHEMIE , INTERNATIONAL EDITION, vol. 50, no. 16, 2011, pages 3793 - 3798
FIELDS, ROY ET AL.: "Metal carbonyl chemistry. IX. Improved syntheses and some reactions of tetracarbonylcyclooctafluorotetramethyleneiron", JOURNAL OF THE CHEMICAL SOCIETY [SECTION] A: INORGANIC, PHYSICAL, THEORETICAL, 1970, pages 1964 - 9
BRUNNER, HENRI ET AL.: "Asymmetric catalysis. XXXVII. Complexes with free donor groups as co- catalysts for enantioselective hydrosilylation", JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol. 335, no. 1, 1987, pages 15 - 27
HUGHES, RUSSE LL P. ET AL.: "Fluoroalkylation of cobalt complexes: selective reactions at the metal or the cyclopentadienyl ring", JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol. 548, no. 1, 1997, pages 109 - 112
MARCHESE, A. L. ET AL.: "Perfluoroalkyl derivatives of chromium and cobalt containing sulfur donor ligands", JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol. 121, no. 1, 1976, pages 63 - 71
TREICHEL, P. M. ET AL.: "Ionic perfluoroalkyl complexes of cobalt", INORGANIC CHEMISTRY, vol. 4, no. 8, 1965, pages 1098 - 102
HU , CHANGMING ET AL.: "Cobaloxime-catalyzed hydroperfluoroalkylation of electron-deficient alkenes with perfluoroalkyl halides: reaction and mechanism", JOURNAL OF ORGANIC CHEMISTRY, vol. 57, no. 12, 1992, pages 3339 - 42
FUKUHARA, TADAHITO ET AL.: "Polyfluorination using IF5", JOURNAL OF ORGANIC CHEMISTRY, vol. 75, no. 21, 2010, pages 7393 - 7399
MOBBS, R. H.: "Heptafluorobenzyl bromide", JOURNAL OF FLUORINE CHEMISTRY, vol. 1, no. 3, 1972, pages 361 - 4
YAGUPOL'SKII, L. M. ET AL.: "Effect of substituents having a trifluoromethyl group on the reactivity of aromatic compounds", ZHURNAL OBSHCHEI KHIMII, vol. 34, no. 11, 1964, pages 3682 - 90
KNUNYANTS, I. L. ET AL.: "omega- Phenylperfluoroolefins and omega- phenylperfluorocarboxylic acids", IZVESTIYA AKADEMII NAUK SSSR, SERIYA KHIMICHESKAYA, 1967, pages 74 - 8
HIROKI SAIJO ET AL.: "Cu(I) o Mochiita TFE eno 1,2-Aryl Fuka Hanno ni yoru ArCF2CF2Ar' Goseiho no Kaihatsu", ABSTRACTS OF THE FLUORINE CONFERENCE OF JAPAN, vol. 36TH, 3 October 2013 (2013-10-03), pages 142 - 143
HIROKI SAIJO ET AL.: "Cu(I) o Mochiita Tetrafluoroethylene no 1,2-Diaryl Fuka Hanno", CSJ: THE CHEMICAL SOCIETY OF JAPAN DAI 94 SHUNKI NENKAI KOEN YOKOSHU IV, vol. 94TH, 12 March 2014 (2014-03-12), pages 1227 - 2 B1-06
Attorney, Agent or Firm:
SAEGUSA & PARTNERS (JP)
Patent business corporation 3 Edakuni [Hajime] patent firm (JP)
Patent business corporation 3 Edakuni [Hajime] patent firm (JP)
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