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dc.contributor.authorBuchanan, Helena S.
dc.contributor.authorPauff, Steven M.
dc.contributor.authorKosmidis, Tilemachos D.
dc.contributor.authorTaladriz-Sender, Andrea
dc.contributor.authorRutherford, Olivia I.
dc.contributor.authorHatit, Marine Z. C.
dc.contributor.authorFenner, Sabine
dc.contributor.authorWatson, Allan J. B.
dc.contributor.authorBurley, Glenn A.
dc.date.accessioned2018-02-06T15:30:33Z
dc.date.available2018-02-06T15:30:33Z
dc.date.issued2017-07-21
dc.identifier.citationBuchanan , H S , Pauff , S M , Kosmidis , T D , Taladriz-Sender , A , Rutherford , O I , Hatit , M Z C , Fenner , S , Watson , A J B & Burley , G A 2017 , ' Modular,step-efficient palladium-catalyzed cross-coupling strategy to access C6-heteroaryl 2-aminopurine ribonucleosides ' , Organic Letters , vol. 19 , no. 14 , pp. 3759-3762 . https://doi.org/10.1021/acs.orglett.7b01602en
dc.identifier.issn1523-7060
dc.identifier.otherPURE: 252194070
dc.identifier.otherPURE UUID: 5e20c732-f256-43ce-acc7-ff547c842c07
dc.identifier.otherRIS: urn:D71D645F98CB90E11C2D33114717DA2D
dc.identifier.otherScopus: 85025166806
dc.identifier.otherORCID: /0000-0002-1582-4286/work/56639172
dc.identifier.urihttp://hdl.handle.net/10023/12680
dc.descriptionThis work was supported by an EPSRC-GSK industrial CASE studentship for H.B., a University studentship for T.D.K., and postdoctoral funding for S.P. by the Leverhulme Trust (RPG-2014-313).en
dc.description.abstractTwo Pd-catalyzed methods to access 6-heteroaryl 2-aminopurine ribonucleosides from 6-chloroguanosine are described. First, Pd-132-catalyzed Suzuki–Miyaura cross-coupling using a series of boron substrates and 6-chloroguanosine forms 6-heteroaryl-2-aminopurines in a single step. The versatility of 6-chloroguanosine is further demonstrated using a modified Sonogashira coupling employing potassium iodide as an additive. Finally, the utility of the 6-alkynyl-2-aminopurine ribonucleoside as a dipolarophile in [3 + 2] cycloadditions is presented, affording triazoles and isoxazoles when reacted with azide and isonitrile 1,3-dipoles, respectively.
dc.format.extent4
dc.language.isoeng
dc.relation.ispartofOrganic Lettersen
dc.rights© 2017 American Chemical Society. This is an open access article published under a Creative Commons Attribution (CC-BY) License, which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.en
dc.subjectQD Chemistryen
dc.subjectNDASen
dc.subject.lccQDen
dc.titleModular,step-efficient palladium-catalyzed cross-coupling strategy to access C6-heteroaryl 2-aminopurine ribonucleosidesen
dc.typeJournal articleen
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews.School of Chemistryen
dc.identifier.doihttps://doi.org/10.1021/acs.orglett.7b01602
dc.description.statusPeer revieweden


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