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dc.contributor.authorHicks, Jamie
dc.contributor.authorVasko, Petra
dc.contributor.authorHeilmann, Andreas
dc.contributor.authorGoicoechea, Jose
dc.contributor.authorAldridge, Simon
dc.date.accessioned2020-07-30T06:10:02Z
dc.date.available2020-07-30T06:10:02Z
dc.date.issued2020
dc.identifier.citationHicks, J., Vasko, P., Heilmann, A., Goicoechea, J., & Aldridge, S. (2020). Arene C‐H activation at aluminium(I) : meta selectivity driven by the electronics of SNAr chemistry. <i>Angewandte Chemie</i>, <i>59</i>(46), 20376-20380. <a href="https://doi.org/10.1002/anie.202008557" target="_blank">https://doi.org/10.1002/anie.202008557</a>
dc.identifier.otherCONVID_41659921
dc.identifier.urihttps://jyx.jyu.fi/handle/123456789/71279
dc.description.abstractThe reactivity of the electron-rich anionic Al(I) (‘aluminyl’) compound K 2 [(NON)Al] 2 (NON = 4,5-bis(2,6-diisopropylanilido)-2,7-di- tert -butyl-9,9-dimethylxanthene) towards mono- and disubstituted arenes is reported. C-H activation chemistry with n -butylbenzene gives exclusively the product of activation at the arene meta position. Mechanistically, this transformation proceeds in a single step via a concerted Meisenheimer-type transition state. Selectivity is therefore based on similar electronic factors to classical S N Ar chemistry, which implies the destabilization of transition states featuring electron-donating groups in either the ortho or the para positions. In the cases of toluene and the three isomers of xylene, benzylic C-H activation is also possible, with the product(s) formed reflecting the feasibility (or otherwise) of competing arene C-H activation at a site which is neither ortho or para to a methyl substituent.en
dc.format.mimetypeapplication/pdf
dc.languageeng
dc.language.isoeng
dc.publisherWiley
dc.relation.ispartofseriesAngewandte Chemie
dc.rightsCC BY-NC 4.0
dc.subject.otheraluminium
dc.subject.otheraluminyl nucleophile
dc.subject.otherC-H activation
dc.subject.otherarenes
dc.subject.otherSNAr mechanism
dc.titleArene C‐H activation at aluminium(I) : meta selectivity driven by the electronics of SNAr chemistry
dc.typearticle
dc.identifier.urnURN:NBN:fi:jyu-202007305427
dc.contributor.laitosKemian laitosfi
dc.contributor.laitosDepartment of Chemistryen
dc.contributor.oppiaineEpäorgaaninen ja analyyttinen kemiafi
dc.contributor.oppiaineInorganic and Analytical Chemistryen
dc.type.urihttp://purl.org/eprint/type/JournalArticle
dc.description.reviewstatuspeerReviewed
dc.format.pagerange20376-20380
dc.relation.issn1433-7851
dc.relation.numberinseries46
dc.relation.volume59
dc.type.versionacceptedVersion
dc.rights.copyright 2020 The Authors.
dc.rights.accesslevelopenAccessfi
dc.relation.grantnumber314794
dc.subject.ysoalumiini
dc.format.contentfulltext
jyx.subject.urihttp://www.yso.fi/onto/yso/p19563
dc.rights.urlhttps://creativecommons.org/licenses/by-nc/4.0/
dc.relation.doi10.1002/anie.202008557
dc.relation.funderSuomen Akatemiafi
dc.relation.funderAcademy of Finlanden
jyx.fundingprogramTutkijatohtori, SAfi
jyx.fundingprogramPostdoctoral Researcher, AoFen
jyx.fundinginformationWe thank the Leverhulme Trust (RP-2018-246) for funding aspects of this work. PV thanks the Academy of Finland (Grant No. 314794) and Prof Heikki Tuononen for providing computational resources


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