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dc.contributor.authorBastick, Kane
dc.contributor.authorWatson, Allan John Bell
dc.date.accessioned2023-08-21T08:30:11Z
dc.date.available2023-08-21T08:30:11Z
dc.date.issued2023-08-15
dc.identifier.citationBastick , K & Watson , A J B 2023 , ' Pd-catalyzed homologation of arylboronic acids as a platform for the diversity-orientated synthesis of benzylic C–X bonds ' , Synlett , vol. 34 , pp. A-F . https://doi.org/10.1055/a-2117-9878en
dc.identifier.issn0936-5214
dc.identifier.otherPURE: 289232416
dc.identifier.otherPURE UUID: f01dd13f-cd19-4f7e-bef1-9ca9e24bbf53
dc.identifier.otherORCID: /0000-0002-1582-4286/work/141228633
dc.identifier.otherScopus: 85164999876
dc.identifier.urihttps://hdl.handle.net/10023/28206
dc.descriptionFunding: K.A.C.B thanks the Engineering and Physical Sciences Research Council (EPSRC, Grant Number EP/W007517/1) and the University of St Andrews for a PhD studentship. A.J.B.W. thanks the Leverhulme Trust for a Research Fellowship and the EPSRC Programme Grant ‘Boron: Beyond the Reagent’ for support. Leverhulme Trust (RF-202-014), University of St Andrews Engineering and PhysicalSciences Research Council (EP/W007517/1).en
dc.description.abstractWe report a synthetic platform for the formation of benzylic C–X bonds. Benzylboronic acid pinacol (Bpin) esters are useful synthetic intermediates but are commercially uncommon, leading to preparations that typically rely upon stoichiometric metalation. Pd-catalyzed formal homologation of arylboronic acids provides access to these compounds that, in turn, allow the formation of C–C, C–O, and C–N bonds from Pd- and Cu-mediated cross-coupling or oxidative processes. This affords a wide variety of benzylic alcohols, diarylmethanes, benzyl amines, and benzyl ethers. Limitations are disclosed and the utility is further demonstrated by the generation of analogues of meclizine.
dc.format.extent6
dc.language.isoeng
dc.relation.ispartofSynletten
dc.rightsCopyright © 2023 The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/).en
dc.subjectBoron catalysisen
dc.subjectChemoselectivityen
dc.subjectHomologationen
dc.subjectDiversity-oriented synthesisen
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subjectMCCen
dc.subject.lccQDen
dc.titlePd-catalyzed homologation of arylboronic acids as a platform for the diversity-orientated synthesis of benzylic C–X bondsen
dc.typeJournal articleen
dc.contributor.sponsorThe Leverhulme Trusten
dc.contributor.sponsorUK Research and Innovationen
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.contributor.institutionUniversity of St Andrews. Sir James Mackenzie Institute for Early Diagnosisen
dc.identifier.doihttps://doi.org/10.1055/a-2117-9878
dc.description.statusPeer revieweden
dc.identifier.grantnumberRF-2022-014en
dc.identifier.grantnumberEP/W007517/1en


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