Title:
NAPHTHYL SILOLE PRODUCTION METHOD, NAPHTHYL SILOLE HAVING HETEROCYCLIC GROUP, AND GRAPHENE NANORIBBONS HAVING HETEROCYCLIC GROUP
Document Type and Number:
WIPO Patent Application WO/2021/177144
Kind Code:
A1
Abstract:
Provided is a method which makes it possible to more safely produce a naphthyl silole to be used as a GNR raw material, by: producing a lanthanoid complex of a compound represented by formula (1) by reacting the compound represented by formula (1) with a lanthanoid and a lithium-containing ate complex; and thereafter, reacting the lanthanoid complex with a silyl compound represented by formula (2).
(1)
(In the formula, R1a and R1b are identical or different, and each represent a hydrogen atom, an alkyl group, a cycloalkyl group, a (poly)ether group, an ester group, a halogen atom, an aromatic hydrocarbon group, a heterocyclic group; R1a and R1b are bonded to each other and may form a ring; R2 represents an aromatic hydrocarbon group or a heterocyclic group; and X represents a bromine atom or an iodine atom.)
(2): R3aR3bSiCl2
(In the formula, R3a and R3b are identical or different and each represent a phenyl group or an alkyl group that has 1-4 carbon atoms and may have a branch.)
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Inventors:
ITAMI KENICHIRO (JP)
ITO HIDETO (JP)
MATSUSHIMA KAHO (JP)
MURAKAMI KAZUO (JP)
NAKATSUJI HIDEFUMI (JP)
ISHIDA SHUNSUKE (JP)
ITO HIDETO (JP)
MATSUSHIMA KAHO (JP)
MURAKAMI KAZUO (JP)
NAKATSUJI HIDEFUMI (JP)
ISHIDA SHUNSUKE (JP)
Application Number:
PCT/JP2021/007201
Publication Date:
September 10, 2021
Filing Date:
February 25, 2021
Export Citation:
Assignee:
NATIONAL UNIV CORPORATION TOKAI NATIONAL HIGHER EDUCATION AND RESEARCH SYSTEM (JP)
TAOKA CHEMICAL CO LTD (JP)
TAOKA CHEMICAL CO LTD (JP)
International Classes:
C07F7/08; C07B61/00; C07C17/263; C07C25/22; C07C309/65
Domestic Patent References:
| WO2008156052A1 | 2008-12-24 | |||
| WO2019102936A1 | 2019-05-31 | |||
| WO2012083171A1 | 2012-06-21 | |||
| WO2010038956A2 | 2010-04-08 | |||
| WO2014126241A1 | 2014-08-21 | |||
| WO2020184625A1 | 2020-09-17 |
Foreign References:
| JP2014019671A | 2014-02-03 | |||
| JP2014019679A | 2014-02-03 | |||
| CN107652287A | 2018-02-02 | |||
| KR20160076931A | 2016-07-01 | |||
| US20170141331A1 | 2017-05-18 | |||
| KR20150042386A | 2015-04-21 | |||
| US20150325799A1 | 2015-11-12 | |||
| US20180053902A1 | 2018-02-22 | |||
| CN106543215A | 2017-03-29 | |||
| CN110204691A | 2019-09-06 | |||
| JP2021011471A | 2021-02-04 |
Other References:
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MOCHIDA KENJI, SHIMIZU MASAKI, HIYAMA TAMEJIRO: "Palladium-Catalyzed Intramolecular Coupling of 2-[(2-Pyrrolyl)silyl]aryl Triflates through 1,2-Silicon Migration", J. AM. CHEM. SOC., vol. 131, no. 24, 2009, pages 8350 - 8351, XP055852576
WEI BAOSHENG, ZHANG DONGCHAO, CHEN YI‐HUNG, LEI AIWEN, KNOCHEL PAUL: "Preparation of polyfunctional biaryl derivatives by cyclolanthanation of 2-bromobiaryls and heterocyclic analogues using nBu2LaCl.4LiCl", ANGEW. CHEM. INT. ED, vol. 58, no. 44, 2019, pages 15631 - 15635, XP055852571
MCCONACHIE, L. K ET AL.: "A novel base-induced cyclization of selected benzyl alkynyl sulfides for the synthesis of 2-aryl-2, 3-dihydrothiophenes", TETRAHEDRON LETTERS, vol. 41, no. 30, 2000, pages 5637 - 5641, XP004209529, DOI: 10.1016/S0040-4039(00)00916-3
BARLUENGA JOSÉ, VÁZQUEZ-VILLA HENAR, MERINO ISABEL, BALLESTEROS ALFREDO, GONZÁLEZ JOSÉ M.: "The reaction of o-alkynylarene and heteroarene carboxaldehyde derivatives with iodonium ions and nucleophiles: a versatile and regioselective synthesis of 1H-isochromene, naphthalene, indole, benzofuran, and benzothiophene compounds", CHEMISTRY-A EUROPEAN JOURNAL, vol. 12, no. 22, 2006, pages 5790 - 5805, XP055852564
DONG, C. G ET AL.: "Pd(OAc) 2-catalyzed domino reactions of 1, 2-dihaloarenes and 2-haloaryl arenesulfonates with Grignard reagents: efficient synthesis of substituted fluorenes", TETRAHEDRON, vol. 64, no. 11, 2008, pages 2537 - 2552, XP022454904, DOI: 10.1016/j.foreco.2007.08.002
MOCHIDA KENJI, SHIMIZU MASAKI, HIYAMA TAMEJIRO: "Palladium-Catalyzed Intramolecular Coupling of 2-[(2-Pyrrolyl)silyl]aryl Triflates through 1,2-Silicon Migration", J. AM. CHEM. SOC., vol. 131, no. 24, 2009, pages 8350 - 8351, XP055852576
WEI BAOSHENG, ZHANG DONGCHAO, CHEN YI‐HUNG, LEI AIWEN, KNOCHEL PAUL: "Preparation of polyfunctional biaryl derivatives by cyclolanthanation of 2-bromobiaryls and heterocyclic analogues using nBu2LaCl.4LiCl", ANGEW. CHEM. INT. ED, vol. 58, no. 44, 2019, pages 15631 - 15635, XP055852571
Attorney, Agent or Firm:
SAEGUSA & PARTNERS (JP)
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