Synthesis of Benzoisoselenazolones via Rh(III)-Catalyzed Direct Annulative Selenation by Using Elemental Selenium

Xu-Xu, Qing Feng; Nishii, Yuji; Uetake, Yuta; Sakurai, Hidehiro; Miura, Masahiro

doi:https://doi.org/10.1002/chem.202103485

Synthesis of Benzoisoselenazolones via Rh(III)-Catalyzed Direct Annulative Selenation by Using Elemental Selenium

Xu-Xu, Qing Feng; Nishii, Yuji; Uetake, Yuta et al.

Chemistry - A European Journal, 2021, 27(71), 17952-17959

アクセス数:497件（2025-07-19 11:33 集計）

固定URL: https://hdl.handle.net/11094/92779

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タイトル	Synthesis of Benzoisoselenazolones via Rh(III)-Catalyzed Direct Annulative Selenation by Using Elemental Selenium
著者	著者名 Xu-Xu, Qing Feng
	NRID 1000070773787 1000070773787 ORCID 0000-0002-6824-0639 0000-0002-6824-0639 researchmap permalink y_nishii y_nishii Scopus Author ID 55233363700 55233363700 著者名 Nishii, Yuji
	NRID 1000010755440 1000010755440 ORCID 0000-0002-4742-8085 0000-0002-4742-8085 researchmap permalink yutauetake yutauetake Scopus Author ID 56417952700 56417952700 著者名 Uetake, Yuta
	NRID 1000000262147 1000000262147 ORCID 0000-0001-5783-4151 0000-0001-5783-4151 researchmap permalink read0184917 read0184917 Scopus Author ID 7402869823 7402869823 著者名 Sakurai, Hidehiro
	NRID 1000020183626 1000020183626 ORCID 0000-0001-8288-6439 0000-0001-8288-6439 researchmap permalink read0013936 read0013936 Scopus Author ID 7402799909 7402799909 著者名 Miura, Masahiro
キーワード等	annulation
	benzoisoselenazolone
	C−H functionalization
	rhodium catalysis
	selenium
内容	This is the accepted version of the following article: Xu-Xu Q.F., Nishii Y., Uetake Y., et al. Synthesis of Benzoisoselenazolones via Rh(III)-Catalyzed Direct Annulative Selenation by Using Elemental Selenium. Chemistry - A European Journal 27, 17952 (2021); which has been published in final form at https://doi.org/10.1002/chem.202103485. This article may be used for non-commercialpurposes in accordance with the Wiley Self-ArchivingPolicy [https://authorservices.wiley.com/author-resources/Journal-Authors/licensing/self-archiving.html]
抄録	Isoselenazolone derivatives have attracted significant research interest because of their potent therapeutic activities and indispensable applications in organic synthesis. Efficient construction of functionalized isoselenazolone scaffolds is still challenging, and thus new synthetic approaches with improved operational simplicity have been of particular interest. In this manuscript, we introduce a rhodium-catalyzed direct selenium annulation by using stable and tractable elemental selenium. A series of benzamides as well as acrylamides were successfully coupled with selenium under mild reaction conditions, and the obtained isoselenazolones could be pivotal synthetic precursors for several organoselenium compounds. Based on the designed control experiments and X-ray absorption spectroscopy measurements, we propose an unprecedented selenation mechanism involving a highly electrophilic Se(IV) species as the reactive selenium donor. The reaction mechanism was further verified by a computational study.
出版者	John Wiley and Sons Inc
収録物名	Chemistry - A European Journal
巻(号)	27(71)
ページ	17952-17959
刊行年月	2021-12-20
言語	英語
ハンドルURL	https://hdl.handle.net/11094/92779
PISSN	09476539
eISSN	15213765
NCID	AA11076269
関連情報 (isVersionOf)	DOI (出版社版) https://doi.org/10.1002/chem.202103485
アクセス権	open access
権利情報	© 2021 Wiley-VCH GmbH
出版タイプ	Accepted Manuscript
カテゴリ	学術雑誌論文 Journal Article

資源タイプ	学術雑誌論文
ローカル資源タイプ	学術雑誌論文
DCMI資源タイプ	text
DCTERMS.bibliographicCitation	Chemistry - A European Journal. 2021, 27(71), p. 17952-17959
DC.title	Synthesis of Benzoisoselenazolones via Rh(III)-Catalyzed Direct Annulative Selenation by Using Elemental Selenium
DC.creator	Xu-Xu, Qing Feng
	Nishii, Yuji
	Uetake, Yuta
	Sakurai, Hidehiro
	Miura, Masahiro
DC.publisher	John Wiley and Sons Inc
DC.language' scheme='DCTERMS.RFC1766	英語
DC.type' scheme='DCTERMS.DCMIType	text
DCTERMS.issued' scheme='DCTERMS.W3CDTF	2021-12-20
DC.identifier	https://doi.org/10.1002/chem.202103485
DC.subject	annulation
	benzoisoselenazolone
	C−H functionalization
	rhodium catalysis
	selenium
DC.description	This is the accepted version of the following article: Xu-Xu Q.F., Nishii Y., Uetake Y., et al. Synthesis of Benzoisoselenazolones via Rh(III)-Catalyzed Direct Annulative Selenation by Using Elemental Selenium. Chemistry - A European Journal 27, 17952 (2021); which has been published in final form at https://doi.org/10.1002/chem.202103485. This article may be used for non-commercialpurposes in accordance with the Wiley Self-ArchivingPolicy [https://authorservices.wiley.com/author-resources/Journal-Authors/licensing/self-archiving.html]
DCTERMS.abstract	Isoselenazolone derivatives have attracted significant research interest because of their potent therapeutic activities and indispensable applications in organic synthesis. Efficient construction of functionalized isoselenazolone scaffolds is still challenging, and thus new synthetic approaches with improved operational simplicity have been of particular interest. In this manuscript, we introduce a rhodium-catalyzed direct selenium annulation by using stable and tractable elemental selenium. A series of benzamides as well as acrylamides were successfully coupled with selenium under mild reaction conditions, and the obtained isoselenazolones could be pivotal synthetic precursors for several organoselenium compounds. Based on the designed control experiments and X-ray absorption spectroscopy measurements, we propose an unprecedented selenation mechanism involving a highly electrophilic Se(IV) species as the reactive selenium donor. The reaction mechanism was further verified by a computational study.
DC.rights	© 2021 Wiley-VCH GmbH
DC.format	92779
citation_title	Synthesis of Benzoisoselenazolones via Rh(III)-Catalyzed Direct Annulative Selenation by Using Elemental Selenium
citation_author	Xu-Xu, Qing Feng
	Nishii, Yuji
	Uetake, Yuta
	Sakurai, Hidehiro
	Miura, Masahiro
citation_publisher	John Wiley and Sons Inc
citation_language	英語
citation_date	2021-12-20
citation_journal_title	Chemistry - A European Journal
citation_volume	27
citation_issue	71
citation_firstpage	17952
citation_lastpage	17959
citation_doi	https://doi.org/10.1002/chem.202103485
citation_public_url	https://hdl.handle.net/11094/92779

Synthesis of Benzoisoselenazolones via Rh(III)-Catalyzed Direct Annulative Selenation by Using Elemental Selenium

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