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dc.contributor.authorWeidlich, Frauke
dc.contributor.authorEsumi, Naoto
dc.contributor.authorChen, Dongyang
dc.contributor.authorMück-Lichtenfeld, Christian
dc.contributor.authorZysman-Colman, Eli
dc.contributor.authorStuder, Armido
dc.date.accessioned2020-11-08T00:39:11Z
dc.date.available2020-11-08T00:39:11Z
dc.date.issued2019-11-08
dc.identifier.citationWeidlich , F , Esumi , N , Chen , D , Mück-Lichtenfeld , C , Zysman-Colman , E & Studer , A 2019 , ' Mild C–F activation in perfluorinated arenes through photosensitized insertion of isonitriles at 350 nm ' , Advanced Synthesis & Catalysis , vol. Early View . https://doi.org/10.1002/adsc.201901126en
dc.identifier.issn1615-4150
dc.identifier.otherPURE: 262877627
dc.identifier.otherPURE UUID: e1a0bfd5-ff74-465f-b050-f5d259586cc4
dc.identifier.otherRIS: urn:5A9641CB851D9EB5899BFE139119A825
dc.identifier.otherORCID: /0000-0001-7183-6022/work/64697943
dc.identifier.otherScopus: 85074882550
dc.identifier.otherWOS: 000495135500001
dc.identifier.urihttp://hdl.handle.net/10023/20923
dc.descriptionAuthors thank the Westfälische Wilhelms-University of Münster for continuous financial support.en
dc.description.abstractFluorinated compounds have become important in the fields of agrochemical industry, pharmaceutical chemistry and materials sciences. Accordingly, various methods for their preparation have been developed in the past. Fluorinated compounds can be accessed via conjugation with fluorinated building blocks, via C–H fluorination or via selective activation of perfluorinated compounds to give the partially fluorinated congeners. Especially the direct activation of C–F bonds, one of the strongest σ‐bonds, still remains challenging and new strategies for C–F activation are desirable. Herein a method for the photochemical activation of aromatic C–F bonds is presented. It is shown that isonitriles selectively insert into aromatic C–F bonds while aliphatic C–F bonds remain unaffected. Mechanistic studies reveal the reaction to proceed via the indirect excitation of the isonitrile to its triplet state by photoexcited acetophenone at 350 nm. Due to the relatively mild light used, the process shows high functional group tolerance and various compounds of the class of benzimidoyl fluorides are accessible from aryl isonitriles and commercially available perfluorinated arenes.
dc.language.isoeng
dc.relation.ispartofAdvanced Synthesis & Catalysisen
dc.rightsCopyright © 2019 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim. This work has been made available online in accordance with publisher policies or with permission. Permission for further reuse of this content should be sought from the publisher or the rights holder. This is the author created accepted manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1002/adsc.201901126en
dc.subjectPhotochemistryen
dc.subjectSensitizersen
dc.subjectInsertionen
dc.subjectFluorineen
dc.subjecttransition-metal freeen
dc.subjectC–F activationen
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subject.lccQDen
dc.titleMild C–F activation in perfluorinated arenes through photosensitized insertion of isonitriles at 350 nmen
dc.typeJournal articleen
dc.description.versionPostprinten
dc.contributor.institutionUniversity of St Andrews.School of Chemistryen
dc.contributor.institutionUniversity of St Andrews.EaSTCHEMen
dc.identifier.doihttps://doi.org/10.1002/adsc.201901126
dc.description.statusPeer revieweden
dc.date.embargoedUntil2020-11-08


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