Direct Nucleophilic Substitution of Alcohols Using an Immobilized Oxovanadium Catalyst

Nishio, Tomoya; Yoshioka, Shin; Hasegawa, Kai; Yahata, Kenzo; Kanomata, Kyohei; Akai, Shuji

doi:https://doi.org/10.1002/ejoc.202100569

Direct Nucleophilic Substitution of Alcohols Using an Immobilized Oxovanadium Catalyst

Nishio, Tomoya; Yoshioka, Shin; Hasegawa, Kai et al.

European Journal of Organic Chemistry, 2021, 2021(31), 4417-4422

アクセス数:163件（2025-04-14 12:40 集計）

固定URL: https://hdl.handle.net/11094/92243

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タイトル	Direct Nucleophilic Substitution of Alcohols Using an Immobilized Oxovanadium Catalyst
著者	著者名 Nishio, Tomoya
	著者名 Yoshioka, Shin
	著者名 Hasegawa, Kai
	NRID 1000030808100 1000030808100 著者名 Yahata, Kenzo
	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
	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
キーワード等	Heterogeneous catalysis
	Mesoporous silica
	Nucleophilic substitution
	Oxovanadium
	Thioethers
内容	This is the pre-peer reviewed version of the following article:Nishio T., Yoshioka S., Hasegawa K., et al. Direct Nucleophilic Substitution of Alcohols Using an Immobilized Oxovanadium Catalyst. European Journal of Organic Chemistry 2021, 4417 (2021), which has been published in final form at https://doi.org/10.1002/ejoc.202100569. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving
抄録	Direct nucleophilic substitution of alcohols with thiols or carbon nucleophiles was achieved using a mesoporous silica-supported oxovanadium catalyst (VMPS4). Benzyl and allyl alcohols were compatible in this reaction under mild conditions, affording the products in high yields. The VMPS4 catalyst showed excellent chemoselectivity toward alcohols in the presence of acid-labile functional groups, which is in contrast to that observed for the commonly used Lewis acid catalysts, which exhibit poor selectivity. The VMPS4 catalyst could be recycled by simple centrifugation, and the catalytic activity was maintained over seven cycles.
出版者	John Wiley and Sons Inc
収録物名	European Journal of Organic Chemistry
巻(号)	2021(31)
ページ	4417-4422
刊行年月	2021-08-20
言語	英語
ハンドルURL	https://hdl.handle.net/11094/92243
PISSN	1434193X
eISSN	10990690
関連情報 (isVersionOf)	DOI (出版社版) https://doi.org/10.1002/ejoc.202100569
アクセス権	open access
権利情報	This article is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
出版タイプ	Accepted Manuscript
カテゴリ	学術雑誌論文 Journal Article

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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	European Journal of Organic Chemistry. 2021, 2021(31), p. 4417-4422
DC.title	Direct Nucleophilic Substitution of Alcohols Using an Immobilized Oxovanadium Catalyst
DC.creator	Nishio, Tomoya
	Yoshioka, Shin
	Hasegawa, Kai
	Yahata, Kenzo
	Kanomata, Kyohei
	Akai, Shuji
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	2021-08-20
DC.identifier	https://doi.org/10.1002/ejoc.202100569
DC.subject	Heterogeneous catalysis
	Mesoporous silica
	Nucleophilic substitution
	Oxovanadium
	Thioethers
DC.description	This is the pre-peer reviewed version of the following article:Nishio T., Yoshioka S., Hasegawa K., et al. Direct Nucleophilic Substitution of Alcohols Using an Immobilized Oxovanadium Catalyst. European Journal of Organic Chemistry 2021, 4417 (2021), which has been published in final form at https://doi.org/10.1002/ejoc.202100569. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving
DCTERMS.abstract	Direct nucleophilic substitution of alcohols with thiols or carbon nucleophiles was achieved using a mesoporous silica-supported oxovanadium catalyst (VMPS4). Benzyl and allyl alcohols were compatible in this reaction under mild conditions, affording the products in high yields. The VMPS4 catalyst showed excellent chemoselectivity toward alcohols in the presence of acid-labile functional groups, which is in contrast to that observed for the commonly used Lewis acid catalysts, which exhibit poor selectivity. The VMPS4 catalyst could be recycled by simple centrifugation, and the catalytic activity was maintained over seven cycles.
DC.rights	This article is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
DC.format	92243
citation_title	Direct Nucleophilic Substitution of Alcohols Using an Immobilized Oxovanadium Catalyst
citation_author	Nishio, Tomoya
	Yoshioka, Shin
	Hasegawa, Kai
	Yahata, Kenzo
	Kanomata, Kyohei
	Akai, Shuji
citation_publisher	John Wiley and Sons Inc
citation_language	英語
citation_date	2021-08-20
citation_journal_title	European Journal of Organic Chemistry
citation_volume	2021
citation_issue	31
citation_firstpage	4417
citation_lastpage	4422
citation_doi	https://doi.org/10.1002/ejoc.202100569
citation_public_url	https://hdl.handle.net/11094/92243