Title:
PRODUCTION METHOD FOR FLUORINATED AROMATIC SECONDARY AMINE COMPOUND
Document Type and Number:
WIPO Patent Application WO/2020/027258
Kind Code:
A1
Abstract:
By using this production method for a fluorinated aromatic secondary amine compound comprising reacting a fluorinated aromatic primary amine compound with a chlorinated, brominated, or iodinated aromatic hydrocarbon or a pseudohalogenated aromatic hydrocarbon in the presence of a catalyst containing a complex of palladium(0) with dibenzylidine acetone, a ligand represented by formula (L), and a base, it is possible to easily and efficiently produce a secondary amine compound having, in the molecule, a fluoroaryl moiety, by causing a fluorinated aromatic amine compound and a chlorinated, brominated, or iodinated aromatic hydrocarbon or a pseudohalogenated aromatic hydrocarbon to undergo a coupling reaction, without a special catalyst. (Each R1 independently represents an alkyl group having 1-20 carbon atoms or the like, R2-R5 each independently represent a hydrogen atom, an alkyl group having 1-20 carbon atoms, or the like, R6-R8 each independently represent a hydrogen atom, an alkyl group having 1-20 carbon atoms, or the like.)
Inventors:
KOJIMA KEISUKE (JP)
Application Number:
PCT/JP2019/030194
Publication Date:
February 06, 2020
Filing Date:
August 01, 2019
Export Citation:
Assignee:
NISSAN CHEMICAL CORP (JP)
International Classes:
C07C209/10; B01J31/24; C07C211/56; C07D209/86; C08G73/02; H01L51/50; C07B61/00
Foreign References:
| JP2004505091A | 2004-02-19 | |||
| JP2005336083A | 2005-12-08 | |||
| JP2009298773A | 2009-12-24 | |||
| JP2010199250A | 2010-09-09 | |||
| JP2010143979A | 2010-07-01 | |||
| CN107021931A | 2017-08-08 |
Other References:
ZHANG, YAHONG ET AL.: "Influence of the Halogenated Substituent on Charge Transfer Mobility of Aniline Tetramer and Derivatives: Remarkable Anisotropic Mobilities", THE JOURNAL OF PHYSICAL CHEMISTRY C, vol. 121, no. 33, 14 August 2017 (2017-08-14), pages 17633 - 17640, XP055712766, DOI: 10.1021/acs.jpcc.7b04942
KOPPANG, R.: "Disubstitution on hexafluorobenzene with formanilides ", JOURNAL OF FLUORINE CHEMISTRY, vol. 74, no. 2, 1995, pages 177 - 179, XP055712772
COGHI, PAOLO ET AL.: "Reactivity of decafluorobenzophenone and decafluoroazobenzene towards aromatic diamines: a practical entry to donor–acceptor systems", NEW JOURNAL OF CHEMISTRY, vol. 39, no. 5, 2015, pages 3615 - 3623, XP055712775, ISSN: 1144-0546, DOI: 10.1039/C4NJ02359E
CHEMICAL ABSTRACTS, 19 June 2007, Columbus, Ohio, US; abstract no. CAS-937809-63-7, SIN
HILD, FREDERIC ET AL.: "Synthesis and Structural Characterization of Various N,O,N-Chelated Aluminum and Gallium Complexes for the Efficient ROP of Cyclic Esters and Carbonates: How Do Aluminum and Gallium Derivatives Compare ?", ORGANOMETALLICS, vol. 32, no. 2, 11 January 2013 (2013-01-11), pages 587 - 598, XP055712780, DOI: 10.1021/om3011068
KOPPANG, R.: "Disubstitution on hexafluorobenzene with formanilides ", JOURNAL OF FLUORINE CHEMISTRY, vol. 74, no. 2, 1995, pages 177 - 179, XP055712772
COGHI, PAOLO ET AL.: "Reactivity of decafluorobenzophenone and decafluoroazobenzene towards aromatic diamines: a practical entry to donor–acceptor systems", NEW JOURNAL OF CHEMISTRY, vol. 39, no. 5, 2015, pages 3615 - 3623, XP055712775, ISSN: 1144-0546, DOI: 10.1039/C4NJ02359E
CHEMICAL ABSTRACTS, 19 June 2007, Columbus, Ohio, US; abstract no. CAS-937809-63-7, SIN
HILD, FREDERIC ET AL.: "Synthesis and Structural Characterization of Various N,O,N-Chelated Aluminum and Gallium Complexes for the Efficient ROP of Cyclic Esters and Carbonates: How Do Aluminum and Gallium Derivatives Compare ?", ORGANOMETALLICS, vol. 32, no. 2, 11 January 2013 (2013-01-11), pages 587 - 598, XP055712780, DOI: 10.1021/om3011068
Attorney, Agent or Firm:
PATENT PROFESSIONAL CORPORATION EI-MEI PATENT OFFICE (JP)
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