Mechanistic Investigation of a Synthetic Route to Biaryls by the Sigmatropic Rearrangement of Arylsulfonium Species

Yanagi, Tomoyuki; Yorimitsu, Hideki

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http://hdl.handle.net/2433/268765

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DCフィールド	値	言語
dc.contributor.author	Yanagi, Tomoyuki	en
dc.contributor.author	Yorimitsu, Hideki	en
dc.contributor.alternative	柳, 智征	ja
dc.contributor.alternative	依光, 英樹	ja
dc.date.accessioned	2022-03-10T09:07:01Z	-
dc.date.available	2022-03-10T09:07:01Z	-
dc.date.issued	2021-09	-
dc.identifier.uri	http://hdl.handle.net/2433/268765	-
dc.description.abstract	A comprehensive mechanistic investigation was conducted on the coupling reaction of aryl sulfoxides with phenols by means of trif luoroacetic anhydride to yield biaryls. NMR experiments revealed that our previously proposed mechanism, which consists of a cascade of an interrupted Pummerer reaction and a rate-determining [3, 3] sigmatropic rearrangement, is reasonable. The electronic ef fects of the substrates have also been evaluated to elucidate the nature of the rearrangement step. Based on experimental observations and theoretical calculations, w e conclude that the rearrangement is highly asynchronous and stepwise rather than concerted when electron-rich phenols are employed for the reaction.	en
dc.language.iso	eng	-
dc.publisher	Wiley	en
dc.rights	This is the peer reviewed version of the following article: [T. Yanagi, H. Yorimitsu, Chem. Eur. J. 2021, 27, 13450.], which has been published in final form at https://doi.org/10.1002/chem.202101735. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited.	en
dc.rights	The full-text file will be made open to the public on 19 August 2022 in accordance with publisher's 'Terms and Conditions for Self-Archiving'.	en
dc.rights	This is not the published version. Please cite only the published version. この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。	en
dc.subject	aryl sulfoxide	en
dc.subject	DFT calculations	en
dc.subject	mechanisms	en
dc.subject	phenol	en
dc.subject	sigmatropic rearrangement	en
dc.title	Mechanistic Investigation of a Synthetic Route to Biaryls by the Sigmatropic Rearrangement of Arylsulfonium Species	en
dc.type	journal article	-
dc.type.niitype	Journal Article	-
dc.identifier.jtitle	Chemistry – A European Journal	en
dc.identifier.volume	27	-
dc.identifier.issue	53	-
dc.identifier.spage	13450	-
dc.identifier.epage	13456	-
dc.relation.doi	10.1002/chem.202101735	-
dc.textversion	author	-
dc.identifier.pmid	34322930	-
dcterms.accessRights	open access	-
datacite.date.available	2022-08-19	-
datacite.awardNumber	19H00895	-
datacite.awardNumber.uri	https://kaken.nii.ac.jp/ja/grant/KAKENHI-PROJECT-19H00895/	-
dc.identifier.pissn	0947-6539	-
dc.identifier.eissn	1521-3765	-
jpcoar.funderName	日本学術振興会	ja
jpcoar.awardTitle	芳香環の還元的破壊に基づく有機合成	ja
出現コレクション:	学術雑誌掲載論文等

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