Racemization of chiral sulfoxide using an immobilized oxovanadium catalyst

Nishio, Tomoya; Shigemitsu, Hajime; Kida, Toshiyuki; Akai, Shuji; Kanomata, Kyohei

doi:https://doi.org/10.1093/bulcsj/uoae144

Racemization of chiral sulfoxide using an immobilized oxovanadium catalyst

Nishio, Tomoya; Shigemitsu, Hajime; Kida, Toshiyuki et al.

Bulletin of the Chemical Society of Japan, 2024, 98(1), 3651

アクセス数:44件（2025-04-10 08:35 集計）

固定URL: https://hdl.handle.net/11094/99973

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タイトル	Racemization of chiral sulfoxide using an immobilized oxovanadium catalyst
著者	著者名 Nishio, Tomoya
	NRID 1000000791815 1000000791815 ORCID 0000-0002-3104-049X 0000-0002-3104-049X researchmap permalink hajime_shigemitsu hajime_shigemitsu Scopus Author ID 25226105000 25226105000 著者名 Shigemitsu, Hajime
	NRID 1000020234297 1000020234297 researchmap permalink tkida tkida Scopus Author ID 7102598538 7102598538 著者名 Kida, Toshiyuki
	NRID 1000060192457 1000060192457 researchmap permalink shuji_akai shuji_akai Scopus Author ID 7006001526 7006001526 ORCID 0000-0001-9149-8745 0000-0001-9149-8745 著者名 Akai, Shuji
	NRID 1000030880447 1000030880447 ORCID 0000-0002-2251-4665 0000-0002-2251-4665 researchmap permalink kyohei_kanomata kyohei_kanomata Scopus Author ID 39861733600 39861733600 著者名 Kanomata, Kyohei
キーワード等	heterogeneous catalysis,
	radical cation
	redox catalysis
内容	This is a pre-copyedited, author-produced version of an article accepted for publication in Bulletin of the Chemical Society of Japan following peer review. The version of record Nishio Tomoya, Shigemitsu Hajime, Kida Toshiyuki, et al. Racemization of chiral sulfoxide using an immobilized oxovanadium catalyst. Bulletin of the Chemical Society of Japan 98, 3651 (2024) is available online at: https://doi.org/10.1093/bulcsj/uoae144.
抄録	Racemization of optically active compounds is an essential process in asymmetric transformations such as dynamic kinetic resolution and deracemization. In this study, the racemization of chiral sulfoxides under mild thermal conditions was realized using a novel silica-gel-supported oxovanadium catalyst. Specifically, we screened reaction conditions, analyzed the substrate scope, and conducted mechanistic studies of the silica-gel-supported oxovanadium-catalyzed racemization of sulfoxides. The racemization reaction has a wide substrate scope, including alkyl aryl sulfoxides and diaryl sulfoxides. The catalyst could be reused by exploiting its heterogeneous nature. Mechanistic studies suggested that racemization proceeds via the formation of a radical cation intermediate mediated by the oxovanadium(V)/(IV) redox cycle.
出版者	Oxford University Press (OUP)
収録物名	Bulletin of the Chemical Society of Japan
巻(号)	98(1)
ページ	3651
刊行年月	2024-12-28
ハンドルURL	https://hdl.handle.net/11094/99973
PISSN	00092673
eISSN	13480634
関連情報 (isVersionOf)	DOI (出版社版) https://doi.org/10.1093/bulcsj/uoae144
アクセス権	embargoed access
権利情報	© 2025 Chemical Society of Japan
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
DCTERMS.bibliographicCitation	Bulletin of the Chemical Society of Japan. 2024, 98(1), p. 3651
DC.title	Racemization of chiral sulfoxide using an immobilized oxovanadium catalyst
DC.creator	Nishio, Tomoya
	Shigemitsu, Hajime
	Kida, Toshiyuki
	Akai, Shuji
	Kanomata, Kyohei
DC.publisher	Oxford University Press (OUP)
DCTERMS.issued' scheme='DCTERMS.W3CDTF	2024-12-28
DC.identifier	https://doi.org/10.1093/bulcsj/uoae144
DC.subject	heterogeneous catalysis,
	radical cation
	redox catalysis
DC.description	This is a pre-copyedited, author-produced version of an article accepted for publication in Bulletin of the Chemical Society of Japan following peer review. The version of record Nishio Tomoya, Shigemitsu Hajime, Kida Toshiyuki, et al. Racemization of chiral sulfoxide using an immobilized oxovanadium catalyst. Bulletin of the Chemical Society of Japan 98, 3651 (2024) is available online at: https://doi.org/10.1093/bulcsj/uoae144.
DCTERMS.abstract	Racemization of optically active compounds is an essential process in asymmetric transformations such as dynamic kinetic resolution and deracemization. In this study, the racemization of chiral sulfoxides under mild thermal conditions was realized using a novel silica-gel-supported oxovanadium catalyst. Specifically, we screened reaction conditions, analyzed the substrate scope, and conducted mechanistic studies of the silica-gel-supported oxovanadium-catalyzed racemization of sulfoxides. The racemization reaction has a wide substrate scope, including alkyl aryl sulfoxides and diaryl sulfoxides. The catalyst could be reused by exploiting its heterogeneous nature. Mechanistic studies suggested that racemization proceeds via the formation of a radical cation intermediate mediated by the oxovanadium(V)/(IV) redox cycle.
DC.rights	© 2025 Chemical Society of Japan
DC.format	99973
citation_title	Racemization of chiral sulfoxide using an immobilized oxovanadium catalyst
citation_author	Nishio, Tomoya
	Shigemitsu, Hajime
	Kida, Toshiyuki
	Akai, Shuji
	Kanomata, Kyohei
citation_publisher	Oxford University Press (OUP)
citation_date	2024-12-28
citation_journal_title	Bulletin of the Chemical Society of Japan
citation_volume	98
citation_issue	1
citation_firstpage	3651
citation_doi	https://doi.org/10.1093/bulcsj/uoae144
citation_public_url	https://hdl.handle.net/11094/99973

Racemization of chiral sulfoxide using an immobilized oxovanadium catalyst

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