Synthesis of highly condensed phospholes by the Lewis acid-assisted dehydrogenative Mallory reaction under visible light irradiation

Kamiyoshi, Ikki; Kojima, Yuki; Xu, Shibo; Yasui, Kosuke; Nishii, Yuji; Hirano, Koji

doi:https://doi.org/10.1039/d4sc05657d

Synthesis of highly condensed phospholes by the Lewis acid-assisted dehydrogenative Mallory reaction under visible light irradiation

Kamiyoshi, Ikki; Kojima, Yuki; Xu, Shibo et al.

Chemical Science, 2024, 15(48), 20413-20420

Number of Access:72（2025-07-17 20:39 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/101968

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Title	Synthesis of highly condensed phospholes by the Lewis acid-assisted dehydrogenative Mallory reaction under visible light irradiation
Creator	CreatorName Kamiyoshi, Ikki
	ORCID 0009-0000-4796-1536 0009-0000-4796-1536 researchmap permalink yuki_kojima yuki_kojima Scopus Author ID 57218704471 57218704471 CreatorName Kojima, Yuki
	CreatorName Xu, Shibo
	NRID 1000010877640 1000010877640 ORCID 0000-0002-3906-8307 0000-0002-3906-8307 researchmap permalink k_yasui k_yasui CreatorName Yasui, Kosuke
	NRID 1000070773787 1000070773787 ORCID 0000-0002-6824-0639 0000-0002-6824-0639 researchmap permalink y_nishii y_nishii Scopus Author ID 55233363700 55233363700 CreatorName Nishii, Yuji
	NRID 1000070532696 1000070532696 ORCID 0000-0001-9752-1985 0000-0001-9752-1985 researchmap permalink koj koj Scopus Author ID 7402407063 7402407063 CreatorName Hirano, Koji
Description	Kamiyoshi I., Kojima Y., Xu S., et al. Synthesis of highly condensed phospholes by the Lewis acid-assisted dehydrogenative Mallory reaction under visible light irradiation. Chemical Science 15, 20413 (2024); https://doi.org/10.1039/d4sc05657d.
Abstract	A photo-promoted oxidative cyclization, that is, the Mallory reaction of 2,3-diarylbenzophopholes has been developed. With the assistance of Bi(OTf)3 Lewis acid, the reaction proceeds smoothly under visible light irradiation even without any external oxidants. The newly developed dehydrogenative conditions are compatible with various functional groups and substitution patterns, which enables the streamlined synthesis of highly condensed dibenzophosphole derivatives of potent interest in material chemistry. Moreover, experimental and computational studies unveil the detailed reaction mechanism. The preliminary optoelectronic properties of some newly synthesized compounds are also demonstrated.
Publisher	Royal Society of Chemistry
Source Title	Chemical Science
Volume (Issue)	15(48)
Page	20413-20420
Date of Issued	2024-11-14
Language	English
Handle URL	https://hdl.handle.net/11094/101968
PISSN	20416520
eISSN	20416539
Relation.isIdenticalTo	DOI (Publisher Version) https://doi.org/10.1039/d4sc05657d
Access Rights	open access
CopyRight	© 2024 The Author(s). Published by the Royal Society of Chemistry
CopyRight	This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
oaire:version	Version of Record
Category	学術雑誌論文 Journal Article

Resource Type	journal article
Local Type	Journal Article
DCMI Type	Text
DCTERMS.bibliographicCitation	Chemical Science. 2024, 15(48), p. 20413-20420
DC.title	Synthesis of highly condensed phospholes by the Lewis acid-assisted dehydrogenative Mallory reaction under visible light irradiation
DC.creator	Kamiyoshi, Ikki
	Kojima, Yuki
	Xu, Shibo
	Yasui, Kosuke
	Nishii, Yuji
	Hirano, Koji
DC.publisher	Royal Society of Chemistry
DC.language' scheme='DCTERMS.RFC1766	English
DC.type' scheme='DCTERMS.DCMIType	Text
DCTERMS.issued' scheme='DCTERMS.W3CDTF	2024-11-14
DC.identifier	https://doi.org/10.1039/d4sc05657d
DC.description	Kamiyoshi I., Kojima Y., Xu S., et al. Synthesis of highly condensed phospholes by the Lewis acid-assisted dehydrogenative Mallory reaction under visible light irradiation. Chemical Science 15, 20413 (2024); https://doi.org/10.1039/d4sc05657d.
DCTERMS.abstract	A photo-promoted oxidative cyclization, that is, the Mallory reaction of 2,3-diarylbenzophopholes has been developed. With the assistance of Bi(OTf)3 Lewis acid, the reaction proceeds smoothly under visible light irradiation even without any external oxidants. The newly developed dehydrogenative conditions are compatible with various functional groups and substitution patterns, which enables the streamlined synthesis of highly condensed dibenzophosphole derivatives of potent interest in material chemistry. Moreover, experimental and computational studies unveil the detailed reaction mechanism. The preliminary optoelectronic properties of some newly synthesized compounds are also demonstrated.
DC.rights	© 2024 The Author(s). Published by the Royal Society of Chemistry
DC.rights	This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
DC.format	101968
citation_title	Synthesis of highly condensed phospholes by the Lewis acid-assisted dehydrogenative Mallory reaction under visible light irradiation
citation_author	Kamiyoshi, Ikki
	Kojima, Yuki
	Xu, Shibo
	Yasui, Kosuke
	Nishii, Yuji
	Hirano, Koji
citation_publisher	Royal Society of Chemistry
citation_language	English
citation_date	2024-11-14
citation_journal_title	Chemical Science
citation_volume	15
citation_issue	48
citation_firstpage	20413
citation_lastpage	20420
citation_doi	https://doi.org/10.1039/d4sc05657d
citation_public_url	https://hdl.handle.net/11094/101968

Synthesis of highly condensed phospholes by the Lewis acid-assisted dehydrogenative Mallory reaction under visible light irradiation

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