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Mechanism of Cu-catalyzed aryl boronic acid halode-boronation using electrophilic halogen : development of a base-catalyzed Iododeboronation for radiolabeling applications

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dc.contributor.authorMolloy, John
dc.contributor.authorO’Rourke, Kerry
dc.contributor.authorFrias, Carolina
dc.contributor.authorSloan, Nikki
dc.contributor.authorWest, Matthew
dc.contributor.authorPimlott, Sally
dc.contributor.authorSutherland, Andrew
dc.contributor.authorWatson, Allan J. B.
dc.date.accessioned2019-04-26T10:30:01Z
dc.date.available2019-04-26T10:30:01Z
dc.date.issued2019-04-05
dc.identifier.citationMolloy , J , O’Rourke , K , Frias , C , Sloan , N , West , M , Pimlott , S , Sutherland , A & Watson , A J B 2019 , ' Mechanism of Cu-catalyzed aryl boronic acid halode-boronation using electrophilic halogen : development of a base-catalyzed Iododeboronation for radiolabeling applications ' , Organic Letters , vol. 21 , no. 7 , pp. 2488-2492 . https://doi.org/10.1021/acs.orglett.9b00942en
dc.identifier.issn1523-7060
dc.identifier.otherPURE: 258479341
dc.identifier.otherPURE UUID: 343e4049-04fc-4ff9-98ec-7bd38bd7b48c
dc.identifier.otherScopus: 85063948504
dc.identifier.otherWOS: 000464247500118
dc.identifier.otherORCID: /0000-0002-1582-4286/work/62668491
dc.identifier.urihttps://hdl.handle.net/10023/17591
dc.descriptionThe authors are grateful to EPSRC (EP/R511705/1 and a studentship to K.M.O., EP/K503058/1) and the University of Glasgow. We thank the University of St Andrews (M.J.W) and CAPES/Science Without Borders (C.P.F) for PhD studentships.en
dc.description.abstractAn investigation into the mechanism of Cu-catalyzed aryl boronic acid halodeboronation using electrophilic halogen reagents is reported. Evidence is provided to show that this takes place via a boronate-driven ipso-substitution pathway and that Cu is not required for these processes to operate: general Lewis base catalysis is operational. This in turn allows the rational development of a general, simple, and effective base-catalyzed halodeboronation that is amenable to the preparation of 125I-labeled products for SPECT applications.
dc.format.extent5
dc.language.isoeng
dc.relation.ispartofOrganic Lettersen
dc.rightsCopyright © 2019 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.titleMechanism of Cu-catalyzed aryl boronic acid halode-boronation using electrophilic halogen : development of a base-catalyzed Iododeboronation for radiolabeling applicationsen
dc.typeJournal articleen
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.contributor.institutionUniversity of St Andrews. EaSTCHEMen
dc.identifier.doihttps://doi.org/10.1021/acs.orglett.9b00942
dc.description.statusPeer revieweden


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