dc.contributor.author	Kearney, Aoife M.
dc.contributor.author	Murphy, Linda
dc.contributor.author	Murphy, Chloe
dc.contributor.author	Eccles, Kevin S.
dc.contributor.author	Lawrence, Simon E.
dc.contributor.author	Collins, Stuart G.
dc.contributor.author	Maguire, Anita R.
dc.contributor.funder	Irish Research Council	en
dc.contributor.funder	Department of Education, Ireland	en
dc.date.accessioned	2022-01-19T12:55:10Z
dc.date.available	2022-01-19T12:55:10Z
dc.date.issued	2021-03-26
dc.date.updated	2022-01-19T11:59:32Z
dc.description.abstract	The synthesis of a range of novel α-sulfenyl-β-chloroenones from the corresponding α-sulfenylketones, via a NCS mediated chlorination cascade, is described. The scope of the reaction has been investigated and compounds bearing alkyl- and arylthio substituents have been synthesised. In most instances, the Z α-sulfenyl-β-chloroenones were formed as the major products, while variation of the substituent at the β-carbon position led to an alteration in stereoselectivity. Stille cross-coupling with the Z α-sulfenyl-β-chloroenones led to selective formation of Z sulfenyl chalcones, while the E α-sulfenyl-β-chloroenones did not react under the same conditions. Oxidation of the Z α-sulfenyl-β-chloroenones was followed by isomerisation, leading to the E α-sulfinyl-β-chloroenones. Stille cross-coupling with the E α-sulfinyl-β-chloroenones produced the E sulfinyl chalcones. Either the E or Z sulfinyl chalcones can be obtained by altering the sequence of oxidation and Stille cross-coupling.	en
dc.description.sponsorship	Irish Research Council (GOIPG/2018/112); Science Foundation Ireland (12/RC/2275_P2)	en
dc.description.status	Peer reviewed	en
dc.description.version	Published Version	en
dc.format.mimetype	application/pdf	en
dc.identifier.articleid	132091	en
dc.identifier.citation	Kearney, A., Murphy, L., Murphy, C., Eccles, K., Lawrence, S., Collins, S. and Maguire, A., (2021) 'Synthesis and reactivity of α-sulfenyl-β-chloroenones, including oxidation and Stille cross-coupling to form chalcone derivatives', Tetrahedron, 88, 132091 (12 pp). doi: 10.1016/j.tet.2021.132091	en
dc.identifier.doi	10.1016/j.tet.2021.132091	en
dc.identifier.endpage	12	en
dc.identifier.issn	0040-4020
dc.identifier.journaltitle	Tetrahedron	en
dc.identifier.startpage	1	en
dc.identifier.uri	https://hdl.handle.net/10468/12423
dc.identifier.volume	88	en
dc.language.iso	en	en
dc.publisher	Elsevier	en
dc.relation.project	info:eu-repo/grantAgreement/SFI/SFI Research Centres/12/RC/2275/IE/Synthesis and Solid State Pharmaceutical Centre (SSPC)/	en
dc.relation.uri	https://www.sciencedirect.com/science/article/pii/S0040402021002635
dc.rights	© 2021 The Author(s). Published by Elsevier Ltd. This is an open access article under the CC BY license	en
dc.rights.uri	http://creativecommons.org/licenses/by/4.0/	en
dc.subject	Chalcones	en
dc.subject	Chlorination	en
dc.subject	Oxidation	en
dc.subject	Stille cross-coupling	en
dc.subject	Thioamides	en
dc.subject	Transformation	en
dc.subject	Tools	en
dc.subject	α-Sulfenyl-β-chloroenones	en
dc.title	Synthesis and reactivity of alpha-sulfenyl-beta-chloroenones, including oxidation and Stille cross-coupling to form chalcone derivatives	en
dc.type	Article (peer-reviewed)	en

Synthesis and reactivity of alpha-sulfenyl-beta-chloroenones, including oxidation and Stille cross-coupling to form chalcone derivatives

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