Versatile Biaryls and Fused Aromatics through Oxidative Coupling of Hydroquinones with (Hetero)Arenes

Aijima, Takaaki; Ueda, Rina; Nakane, Takanori; Makino, Fumiaki; Ohnishi, Yusuke; Tokunaga, Jin; Nakajima, Keiichiro; Kamino, Shinichiro; Kurisu, Genji; Namba, Keiichi; Nakata, Hiroki; Mogi, Kaiki; Sajiki, Hironao; Akai, Shuji; Sawama, Yoshinari

doi:https://doi.org/10.1002/slct.202400647

Versatile Biaryls and Fused Aromatics through Oxidative Coupling of Hydroquinones with (Hetero)Arenes

Aijima, Takaaki; Ueda, Rina; Nakane, Takanori et al.

ChemistrySelect, 2024, 9(15), e202400647

Number of Access:1,493（2025-08-14 02:43 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/97141

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Title	Versatile Biaryls and Fused Aromatics through Oxidative Coupling of Hydroquinones with (Hetero)Arenes
Creator	CreatorName Aijima, Takaaki
	CreatorName Ueda, Rina
	NRID 1000050794905 1000050794905 ORCID 0000-0003-2697-2767 0000-0003-2697-2767 researchmap permalink tnakane tnakane Scopus Author ID 56985530800 56985530800 CreatorName Nakane, Takanori
	CreatorName Makino, Fumiaki
	CreatorName Ohnishi, Yusuke
	CreatorName Tokunaga, Jin
	CreatorName Nakajima, Keiichiro
	NRID 1000020537237 1000020537237 CreatorName Kamino, Shinichiro
	NRID 1000090294131 1000090294131 ORCID 0000-0002-5354-0807 0000-0002-5354-0807 researchmap permalink read0051718 read0051718 Scopus Author ID 6701675123 6701675123 CreatorName Kurisu, Genji
	NRID 1000030346142 1000030346142 researchmap permalink read0096830 read0096830 CreatorName Namba, Keiichi
	CreatorName Nakata, Hiroki
	CreatorName Mogi, Kaiki
	NRID 1000050275096 1000050275096 CreatorName Sajiki, Hironao
	NRID 1000060192457 1000060192457 researchmap permalink shuji_akai shuji_akai Scopus Author ID 7006001526 7006001526 ORCID 0000-0001-9149-8745 0000-0001-9149-8745 CreatorName Akai, Shuji
	NRID 1000080552413 1000080552413 researchmap permalink sawama sawama Scopus Author ID 6505798196 6505798196 ORCID 0000-0002-9923-2412 0000-0002-9923-2412 CreatorName Sawama, Yoshinari
Subject	Benzoquinones
	Biaryls
	Heterocycles
	Lewis acids
Description	Aijima T., Ueda R., Nakane T., et al. Versatile Biaryls and Fused Aromatics through Oxidative Coupling of Hydroquinones with (Hetero)Arenes. ChemistrySelect 9, e202400647 (2024); https://doi.org/10.1002/slct.202400647.
Abstract	Hydroquinones bearing an electron-withdrawing group at the C2-position can effectively underwent oxidative coupling with (hetero)arenes (e. g., indoles, electron-rich benzene derivatives) in the presence of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) and FeCl3 to produce the corresponding biaryl products. In the present reactions, the DDQ-mediated oxidation of hydroquinone derivatives produce benzoquinone intermediate, which subsequently underwent FeCl3-catalyzed nucleophilic addition of (hetero)arenes to the α,β-unsaturated carbonyl moiety to give the biaryl product in a one-pot manner. Especially, the indole-based biaryl products were further converted into tetracyclic aromatics through DDQ-mediated oxidation followed by FeCl3-catalyzed intramolecular cyclization. Thiophene derivatives were also applicable to give the tetracyclic aromatics. Moreover, the photophysical properties of the indole- and thiophene-based tetracyclic aromatics in the solution and the solid states were investigated.
Publisher	John Wiley and Sons Inc
Source Title	ChemistrySelect
Volume (Issue)	9(15)
Page	e202400647
Date of Issued	2024-04-18
Language	English
Handle URL	https://hdl.handle.net/11094/97141
eISSN	23656549
Relation.isIdenticalTo	DOI (Publisher Version) https://doi.org/10.1002/slct.202400647
Access Rights	open access
CopyRight	This article is licensed under a Creative Commons Attribution 4.0 International License.
oaire:version	Version of Record
Category	学術雑誌論文 Journal Article

Resource Type	journal article
Local Type	Journal Article
DCTERMS.bibliographicCitation	ChemistrySelect. 2024, 9(15), p. e202400647
DC.title	Versatile Biaryls and Fused Aromatics through Oxidative Coupling of Hydroquinones with (Hetero)Arenes
DC.creator	Aijima, Takaaki
	Ueda, Rina
	Nakane, Takanori
	Makino, Fumiaki
	Ohnishi, Yusuke
	Tokunaga, Jin
	Nakajima, Keiichiro
	Kamino, Shinichiro
	Kurisu, Genji
	Namba, Keiichi
	Nakata, Hiroki
	Mogi, Kaiki
	Sajiki, Hironao
	Akai, Shuji
	Sawama, Yoshinari
DC.publisher	John Wiley and Sons Inc
DC.language' scheme='DCTERMS.RFC1766	English
DCTERMS.issued' scheme='DCTERMS.W3CDTF	2024-04-18
DC.identifier	https://doi.org/10.1002/slct.202400647
DC.subject	Benzoquinones
	Biaryls
	Heterocycles
	Lewis acids
DC.description	Aijima T., Ueda R., Nakane T., et al. Versatile Biaryls and Fused Aromatics through Oxidative Coupling of Hydroquinones with (Hetero)Arenes. ChemistrySelect 9, e202400647 (2024); https://doi.org/10.1002/slct.202400647.
DCTERMS.abstract	Hydroquinones bearing an electron-withdrawing group at the C2-position can effectively underwent oxidative coupling with (hetero)arenes (e. g., indoles, electron-rich benzene derivatives) in the presence of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) and FeCl3 to produce the corresponding biaryl products. In the present reactions, the DDQ-mediated oxidation of hydroquinone derivatives produce benzoquinone intermediate, which subsequently underwent FeCl3-catalyzed nucleophilic addition of (hetero)arenes to the α,β-unsaturated carbonyl moiety to give the biaryl product in a one-pot manner. Especially, the indole-based biaryl products were further converted into tetracyclic aromatics through DDQ-mediated oxidation followed by FeCl3-catalyzed intramolecular cyclization. Thiophene derivatives were also applicable to give the tetracyclic aromatics. Moreover, the photophysical properties of the indole- and thiophene-based tetracyclic aromatics in the solution and the solid states were investigated.
DC.rights	This article is licensed under a Creative Commons Attribution 4.0 International License.
DC.format	97141
citation_title	Versatile Biaryls and Fused Aromatics through Oxidative Coupling of Hydroquinones with (Hetero)Arenes
citation_author	Aijima, Takaaki
	Ueda, Rina
	Nakane, Takanori
	Makino, Fumiaki
	Ohnishi, Yusuke
	Tokunaga, Jin
	Nakajima, Keiichiro
	Kamino, Shinichiro
	Kurisu, Genji
	Namba, Keiichi
	Nakata, Hiroki
	Mogi, Kaiki
	Sajiki, Hironao
	Akai, Shuji
	Sawama, Yoshinari
citation_publisher	John Wiley and Sons Inc
citation_language	English
citation_date	2024-04-18
citation_journal_title	ChemistrySelect
citation_volume	9
citation_issue	15
citation_firstpage	e202400647
citation_doi	https://doi.org/10.1002/slct.202400647
citation_public_url	https://hdl.handle.net/11094/97141

Versatile Biaryls and Fused Aromatics through Oxidative Coupling of Hydroquinones with (Hetero)Arenes

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