Direct Synthesis of Benzoselenophene and Benzothiophene Derivatives from 1,1-Diarylethenes and Biaryls by Chalcogen Cation-Mediated Successive Bond Formation

Iwamoto, Hiroki; Kojima, Yuki; Nishimura, Kazutoshi; Yasui, Kosuke; Hirano, Koji

doi:https://doi.org/10.1021/acs.orglett.3c04033

Direct Synthesis of Benzoselenophene and Benzothiophene Derivatives from 1,1-Diarylethenes and Biaryls by Chalcogen Cation-Mediated Successive Bond Formation

Iwamoto, Hiroki; Kojima, Yuki; Nishimura, Kazutoshi et al.

Organic Letters, 2024, 26(5), 1006-1010

Number of Access:382（2025-07-17 20:11 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/95799

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Title	Direct Synthesis of Benzoselenophene and Benzothiophene Derivatives from 1,1-Diarylethenes and Biaryls by Chalcogen Cation-Mediated Successive Bond Formation
Creator	CreatorName Iwamoto, Hiroki
	ORCID 0009-0000-4796-1536 0009-0000-4796-1536 researchmap permalink yuki_kojima yuki_kojima Scopus Author ID 57218704471 57218704471 CreatorName Kojima, Yuki
	CreatorName Nishimura, Kazutoshi
	NRID 1000010877640 1000010877640 ORCID 0000-0002-3906-8307 0000-0002-3906-8307 researchmap permalink k_yasui k_yasui CreatorName Yasui, Kosuke
	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	Iwamoto H., Kojima Y., Nishimura K., et al. Direct Synthesis of Benzoselenophene and Benzothiophene Derivatives from 1,1-Diarylethenes and Biaryls by Chalcogen Cation-Mediated Successive Bond Formation. Organic Letters 26, 1006 (2024); https://doi.org/10.1021/acs.orglett.3c04033.
Abstract	A Tf₂O-mediated sequential C-Se bond-forming reaction of 1,1-diarylethenes and biaryls with methaneselenic acid has been developed. Upon demethylation workup with ethanolamine, the corresponding benzoselenophene derivatives are obtained directly. The related synthesis of benzothiophene derivatives with sodium methanesulfinate is also possible with the unique assistance of the ball milling technique. The active species is considered to be a highly electrophilic chalcogen cation, which enables successive bond formation even at room temperature.
Publisher	American Chemical Society
Source Title	Organic Letters
Volume (Issue)	26(5)
Page	1006-1010
Date of Issued	2024-02-09
Language	English
Handle URL	https://hdl.handle.net/11094/95799
PISSN	15237060
eISSN	15237052
Relation.isVersionOf	DOI (Publisher Version) https://doi.org/10.1021/acs.orglett.3c04033
Access Rights	open access
CopyRight	This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.3c04033.
oaire:version	Accepted Manuscript
Category	学術雑誌論文 Journal Article

Resource Type	journal article
Local Type	Journal Article
DCMI Type	Text
DCTERMS.bibliographicCitation	Organic Letters. 2024, 26(5), p. 1006-1010
DC.title	Direct Synthesis of Benzoselenophene and Benzothiophene Derivatives from 1,1-Diarylethenes and Biaryls by Chalcogen Cation-Mediated Successive Bond Formation
DC.creator	Iwamoto, Hiroki
	Kojima, Yuki
	Nishimura, Kazutoshi
	Yasui, Kosuke
	Hirano, Koji
DC.publisher	American Chemical Society
DC.language' scheme='DCTERMS.RFC1766	English
DC.type' scheme='DCTERMS.DCMIType	Text
DCTERMS.issued' scheme='DCTERMS.W3CDTF	2024-02-09
DC.identifier	https://doi.org/10.1021/acs.orglett.3c04033
DC.description	Iwamoto H., Kojima Y., Nishimura K., et al. Direct Synthesis of Benzoselenophene and Benzothiophene Derivatives from 1,1-Diarylethenes and Biaryls by Chalcogen Cation-Mediated Successive Bond Formation. Organic Letters 26, 1006 (2024); https://doi.org/10.1021/acs.orglett.3c04033.
DCTERMS.abstract	A Tf₂O-mediated sequential C-Se bond-forming reaction of 1,1-diarylethenes and biaryls with methaneselenic acid has been developed. Upon demethylation workup with ethanolamine, the corresponding benzoselenophene derivatives are obtained directly. The related synthesis of benzothiophene derivatives with sodium methanesulfinate is also possible with the unique assistance of the ball milling technique. The active species is considered to be a highly electrophilic chalcogen cation, which enables successive bond formation even at room temperature.
DC.rights	This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.3c04033.
DC.format	95799
citation_title	Direct Synthesis of Benzoselenophene and Benzothiophene Derivatives from 1,1-Diarylethenes and Biaryls by Chalcogen Cation-Mediated Successive Bond Formation
citation_author	Iwamoto, Hiroki
	Kojima, Yuki
	Nishimura, Kazutoshi
	Yasui, Kosuke
	Hirano, Koji
citation_publisher	American Chemical Society
citation_language	English
citation_date	2024-02-09
citation_journal_title	Organic Letters
citation_volume	26
citation_issue	5
citation_firstpage	1006
citation_lastpage	1010
citation_doi	https://doi.org/10.1021/acs.orglett.3c04033
citation_public_url	https://hdl.handle.net/11094/95799

Direct Synthesis of Benzoselenophene and Benzothiophene Derivatives from 1,1-Diarylethenes and Biaryls by Chalcogen Cation-Mediated Successive Bond Formation

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