Title:
METHOD FOR PRODUCING POLYCYCLIC AROMATIC COMPOUND SUBSTITUTED BY ARYL GROUP
Document Type and Number:
WIPO Patent Application WO/2012/169635
Kind Code:
A1
Abstract:
A PAH compound in which a desired position in a C-H bond is directly arylated can be produced in a simple manner by performing a C-H/C-B coupling procedure using a palladium compound, o-chloranil and a specific boron compound. When the substrate and the boron compound are properly selected, it is possible to produce a PAH as mentioned above and having an increased size by performing a ring condensation reaction subsequent to the above-mentioned process. Further, a PAH compound in which a desired position in a C-H bond is directly arylated can also be produced in a simple manner by performing a C-H/C-H cross-coupling procedure using a palladium compound, o-chloranil and a specific aromatic compound. In this case, when the substrate and the aromatic compound are properly selected, it is possible to produce a PAH as mentioned above and having an increased size by performing a ring condensation reaction subsequent to the above-mentioned process.
Inventors:
ITAMI KENICHIRO (JP)
MOCHIDA KENJI (JP)
KAWASUMI KATSUAKI (JP)
SEGAWA YASUTOMO (JP)
KAJINO TOMONORI (JP)
MOCHIDA KENJI (JP)
KAWASUMI KATSUAKI (JP)
SEGAWA YASUTOMO (JP)
KAJINO TOMONORI (JP)
Application Number:
PCT/JP2012/064845
Publication Date:
December 13, 2012
Filing Date:
June 08, 2012
Export Citation:
Assignee:
UNIV NAGOYA NAT UNIV CORP (JP)
ITAMI KENICHIRO (JP)
MOCHIDA KENJI (JP)
KAWASUMI KATSUAKI (JP)
SEGAWA YASUTOMO (JP)
KAJINO TOMONORI (JP)
ITAMI KENICHIRO (JP)
MOCHIDA KENJI (JP)
KAWASUMI KATSUAKI (JP)
SEGAWA YASUTOMO (JP)
KAJINO TOMONORI (JP)
International Classes:
C07C2/86; C07C5/44; C07C15/20; C07C15/30; C07C15/38; C07C17/263; C07C22/08; C07C25/22; C07B61/00
Domestic Patent References:
| WO2004018587A1 | 2004-03-04 |
Foreign References:
| JP2009016693A | 2009-01-22 | |||
| JP2010238924A | 2010-10-21 | |||
| JP2010222268A | 2010-10-07 | |||
| JP2010222261A | 2010-10-07 | |||
| US20040076853A1 | 2004-04-22 | |||
| JPH10189248A | 1998-07-21 | |||
| US20100258791A1 | 2010-10-14 |
Other References:
MATSUDA,T. ET AL.: "Synthesis of Pyrenes by Twofold Hydroarylation of 2,6-Dialkynylbiphenyls", CHEM. LETT., vol. 40, 2011, pages 40 - 41, XP055140581
DUAN, Z. ET AL.: "A Novel Thiophen-Fused Polycyclic Aromatic with a Tetracene Core: Synthesis, Characterization, Optical and Electrochemical Properties", MOLECULES, vol. 16, 27 May 2011 (2011-05-27), pages 4467 - 4481, XP055140584
JOUAITI,A. ET AL.: "Molecular Tectonics: Design of 1-D Coordination Networks Based on Pyrene- Bearing Pyrazolyl Units", EUR. J. INORG. CHEM., 2003, pages 57 - 61, XP055140588
GARCIA-CUADRADO,D. ET AL.: "Proton Abstraction Mechanism for the Palladium-Catalyzed Intramolecular Arylation", J. AM. CHEM. SOC., vol. 128, 2006, pages 1066 - 1067, XP055143144
CHEMICAL ABSTRACTS, vol. 45, no. 16, 1951, Columbus, Ohio, US; abstract no. 7094E-I,7095A, XP055143145
ANTON, U. ET AL.: "Synthesis of n-Alkyl- Substituted Perylenes and Terrylenes via Alkali-Metal Induced Cyclization of Oligonaphthylenes", CHEM. BER., vol. 125, no. 10, 1992, pages 2325 - 2330, XP055143147
MOCHIDA,K. ET AL.: "Direct Arylation of Polycyclic Aromatic Hydrocarbons through Palladium Catalysis", J. AM. CHEM. SOC., vol. 133, 23 June 2011 (2011-06-23), pages 10716 - 10719, XP055143149
ACKERMANN, L.; VICENTE, R.; KAPDTI, A.R., ANGEW. CHEM., INT. ED., vol. 48, 2009, pages 9792
CHEN, X.; ENGLE, K.M.; WANG, D.-H.; YU, J.-Q., ANGEW. CHEM., INT. ED., vol. 48, 2009, pages 5094
KAWAI, H.; KOBAYASHI, Y.; OI, S.; INOUE, Y., CHEM. COMMUN., 2008, pages 1464
LI, C.-W.; WANG, C.-I.; LIAO, H.-Y.; CHAUDHURI, R.; LIU, R.-S., J. ORG. CHEM., vol. 72, 2007, pages 9203
See also references of EP 2730554A4
DUAN, Z. ET AL.: "A Novel Thiophen-Fused Polycyclic Aromatic with a Tetracene Core: Synthesis, Characterization, Optical and Electrochemical Properties", MOLECULES, vol. 16, 27 May 2011 (2011-05-27), pages 4467 - 4481, XP055140584
JOUAITI,A. ET AL.: "Molecular Tectonics: Design of 1-D Coordination Networks Based on Pyrene- Bearing Pyrazolyl Units", EUR. J. INORG. CHEM., 2003, pages 57 - 61, XP055140588
GARCIA-CUADRADO,D. ET AL.: "Proton Abstraction Mechanism for the Palladium-Catalyzed Intramolecular Arylation", J. AM. CHEM. SOC., vol. 128, 2006, pages 1066 - 1067, XP055143144
CHEMICAL ABSTRACTS, vol. 45, no. 16, 1951, Columbus, Ohio, US; abstract no. 7094E-I,7095A, XP055143145
ANTON, U. ET AL.: "Synthesis of n-Alkyl- Substituted Perylenes and Terrylenes via Alkali-Metal Induced Cyclization of Oligonaphthylenes", CHEM. BER., vol. 125, no. 10, 1992, pages 2325 - 2330, XP055143147
MOCHIDA,K. ET AL.: "Direct Arylation of Polycyclic Aromatic Hydrocarbons through Palladium Catalysis", J. AM. CHEM. SOC., vol. 133, 23 June 2011 (2011-06-23), pages 10716 - 10719, XP055143149
ACKERMANN, L.; VICENTE, R.; KAPDTI, A.R., ANGEW. CHEM., INT. ED., vol. 48, 2009, pages 9792
CHEN, X.; ENGLE, K.M.; WANG, D.-H.; YU, J.-Q., ANGEW. CHEM., INT. ED., vol. 48, 2009, pages 5094
KAWAI, H.; KOBAYASHI, Y.; OI, S.; INOUE, Y., CHEM. COMMUN., 2008, pages 1464
LI, C.-W.; WANG, C.-I.; LIAO, H.-Y.; CHAUDHURI, R.; LIU, R.-S., J. ORG. CHEM., vol. 72, 2007, pages 9203
See also references of EP 2730554A4
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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