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dc.contributor.authorMoorthy, Suresh
dc.contributor.authorCastillo, Bonillo Alvaro
dc.contributor.authorLambert, Hugues
dc.contributor.authorKalenius, Elina
dc.contributor.authorLee, Tung-Chun
dc.date.accessioned2022-05-19T07:10:47Z
dc.date.available2022-05-19T07:10:47Z
dc.date.issued2022
dc.identifier.citationMoorthy, S., Castillo, B. A., Lambert, H., Kalenius, E., & Lee, T.-C. (2022). Modulating the reaction pathway of phenyl diazonium ions using host–guest complexation with cucurbit[7]uril. <i>Chemical Communications</i>, <i>58</i>(22), 3617-3620. <a href="https://doi.org/10.1039/d1cc06982a" target="_blank">https://doi.org/10.1039/d1cc06982a</a>
dc.identifier.otherCONVID_104384161
dc.identifier.urihttps://jyx.jyu.fi/handle/123456789/81137
dc.description.abstractAryl diazonium ions are known to be an important intermediate in the divergent synthesis of azo compounds and substituted aromatics. The presence of more than one electrophilic center in a diazonium ion could lead to undesirable side reactions during a synthesis. Herein, we report that the electrophilic α-carbon on a phenyl diazonium [PhN2]+ ion can be selectively deactivated upon host–guest complexation with cucurbit[7]uril (CB7) in aqueous media, achieving a ∼60-fold increase in the half-life of [PhN2]+. Notably, however, the electrophilic nitrogen of the encapsulated diazonium ion remains active towards diazo coupling with strong nucleophiles, allowing the formation of azo compounds using a two-month-old aqueous solution of [CB7–PhN2]+. Our supramolecular approach can open new possibilities for the reactive chemistry of organic molecules in aqueous media.en
dc.format.mimetypeapplication/pdf
dc.language.isoeng
dc.publisherRoyal Society of Chemistry (RSC)
dc.relation.ispartofseriesChemical Communications
dc.rightsCC BY 3.0
dc.titleModulating the reaction pathway of phenyl diazonium ions using host–guest complexation with cucurbit[7]uril
dc.typearticle
dc.identifier.urnURN:NBN:fi:jyu-202205192769
dc.contributor.laitosKemian laitosfi
dc.contributor.laitosDepartment of Chemistryen
dc.contributor.oppiaineOrgaaninen kemiafi
dc.contributor.oppiaineAnalyyttinen kemiafi
dc.contributor.oppiaineNanoscience Centerfi
dc.contributor.oppiaineOrganic Chemistryen
dc.contributor.oppiaineAnalytical Chemistryen
dc.contributor.oppiaineNanoscience Centeren
dc.type.urihttp://purl.org/eprint/type/JournalArticle
dc.type.coarhttp://purl.org/coar/resource_type/c_2df8fbb1
dc.description.reviewstatuspeerReviewed
dc.format.pagerange3617-3620
dc.relation.issn1359-7345
dc.relation.numberinseries22
dc.relation.volume58
dc.type.versionpublishedVersion
dc.rights.copyright© Authors, 2022
dc.rights.accesslevelopenAccessfi
dc.subject.ysosupramolekulaarinen kemia
dc.format.contentfulltext
jyx.subject.urihttp://www.yso.fi/onto/yso/p37759
dc.rights.urlhttps://creativecommons.org/licenses/by/3.0/
dc.relation.doi10.1039/d1cc06982a
jyx.fundinginformationThis work is funded by the Leverhulme Trust (RPG-2016-393). A. C. B. is grateful to the A*STAR-UCL Studentship funded via the EPSRC M3S CDT (EP/L015862/1). We acknowledge the use of the UCL Myriad high performance computing facility, and the UK Materials and Molecular Modelling Hub, which are partially funded by EPSRC (EP/P020194/1).
dc.type.okmA1


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