Access to some C5-cyclised 2 pyrones and 2-pyridones via direct arylation; retention of chloride as a synthetic handle

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dc.contributor.authorMcGlacken, Gerard P.
dc.contributor.authorFairlamb, Ian
dc.contributor.authorPrendergast, Aisling
dc.contributor.authorPardo, Leticia
dc.contributor.funderScience Foundation Irelanden
dc.date.accessioned2017-09-12T09:37:40Z
dc.date.available2017-09-12T09:37:40Z
dc.date.issued2017-08-04
dc.date.updated2017-09-12T09:26:20Z
dc.description.abstractThe synthetic effort towards the functionalisation of C-H bonds on 2 pyrones and 2-pyridones has been funnelled by the preferential reactivity of the C-3 position. Herein, we report a direct arylation protocol for the intramolecular coupling of 2 pyrones and 2 pyridones, allowing access to a previously unavailable class of C-5 cyclised products with an unstudied biological profile. A C-Cl bond was retained at C-3 during the direct arylation process allowing further derivatisation at C-3, which we have demonstrated with a proof-of-principle Suzuki-Miyaura cross-coupling reaction.en
dc.description.sponsorshipScience Foundation Ireland (SFI/12/IP/1315 and SFI/12/RC/2275)en
dc.description.statusPeer revieweden
dc.description.versionAccepted Versionen
dc.format.mimetypeapplication/pdfen
dc.identifier.citationMcGlacken, G. P., Fairlamb, I., Prendergast, A. and Pardo, L. (2017) 'Access to some C5-cyclised 2 pyrones and 2-pyridones via direct arylation; retention of chloride as a synthetic handle', European Journal of Organic Chemistry, 2017(34), pp. 5119-5124. doi:10.1002/ejoc.201700980en
dc.identifier.doi10.1002/ejoc.201700980
dc.identifier.endpage5124
dc.identifier.issn1099-0690
dc.identifier.issued34
dc.identifier.journaltitleEuropean Journal of Organic Chemistryen
dc.identifier.startpage5119
dc.identifier.urihttps://hdl.handle.net/10468/4685
dc.identifier.volume2017
dc.language.isoenen
dc.publisherJohn Wiley & Sons, Ltden
dc.rights© 2017, John Wiley & Sons Ltd. This is the peer reviewed version of the following article: McGlacken, G. P., Fairlamb, I., Prendergast, A. and Pardo, L. (2017) 'Access to some C5-cyclised 2 pyrones and 2-pyridones via direct arylation; retention of chloride as a synthetic handle', European Journal of Organic Chemistry, 2017(34), pp. 5119-5124, which has been published in final form at http://dx.doi.org/ 10.1002/ejoc.201700980. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.en
dc.subjectC-H activationen
dc.subjectCross-couplingen
dc.subjectHeterocyclesen
dc.subjectPalladiumen
dc.subjectSynthetic methodsen
dc.titleAccess to some C5-cyclised 2 pyrones and 2-pyridones via direct arylation; retention of chloride as a synthetic handleen
dc.typeArticle (peer-reviewed)en
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