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A Pd-catalyzed organometallic-free homologation of arylboronic acids enabled by chemoselective transmetalation

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dc.contributor.authorBastick, Kane A. C.
dc.contributor.authorWatson, Allan J. B.
dc.date.accessioned2023-05-12T13:30:02Z
dc.date.available2023-05-12T13:30:02Z
dc.date.issued2023-05-19
dc.identifier285276916
dc.identifier83b92b3e-e00e-49e5-84a9-3dee314c78c7
dc.identifier85160864869
dc.identifier.citationBastick , K A C & Watson , A J B 2023 , ' A Pd-catalyzed organometallic-free homologation of arylboronic acids enabled by chemoselective transmetalation ' , ACS Catalysis , vol. 13 , no. 10 , pp. 7013–7018 . https://doi.org/10.1021/acscatal.3c00921en
dc.identifier.issn2155-5435
dc.identifier.otherORCID: /0000-0002-1582-4286/work/135019328
dc.identifier.urihttps://hdl.handle.net/10023/27599
dc.descriptionFunding: K.A.C.B. thanks EPSRC and the University of St Andrews for a PhD studentship. A.J.B.W. thanks the Leverhulme Trust for a Research Fellowship (RF-2022-014) and the EPSRC Programme Grant “Boron: Beyond the Reagent” (EP/W007517) for support.en
dc.description.abstractA Pd-catalyzed homologation of arylboronic acids is reported. Halomethylboronic acid pinacol esters (Bpin) undergo a remarkably facile, yet rare, oxidative addition enabled by an α-boryl effect. Simultaneous chemoselective transmetalation allows use of these metalloid reagents for formal C1 insertion to deliver benzyl Bpin products without the requirement for stoichiometric organometallic reagents. The utility of the process is demonstrated by stepwise C(sp3)–C(sp2) cross-coupling of the boronic ester products into diarylmethane pharmacophores and electrophile/nucleophile chemoselective cross-coupling. Control experiments that demonstrate the reactivity enhancement provided by the α-boryl effect are provided, along with a description of the limitations of the formal homologation process.
dc.format.extent6
dc.format.extent1884747
dc.language.isoeng
dc.relation.ispartofACS Catalysisen
dc.subjectBoronen
dc.subjectCatalysisen
dc.subjectChemoselectivityen
dc.subjectCross-couplingen
dc.subjectHomologationen
dc.subjectPalladiumen
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subjectMCCen
dc.subject.lccQDen
dc.titleA Pd-catalyzed organometallic-free homologation of arylboronic acids enabled by chemoselective transmetalationen
dc.typeJournal articleen
dc.contributor.sponsorEPSRCen
dc.contributor.sponsorThe Leverhulme Trusten
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.contributor.institutionUniversity of St Andrews. Sir James Mackenzie Institute for Early Diagnosisen
dc.identifier.doi10.1021/acscatal.3c00921
dc.description.statusPeer revieweden
dc.identifier.grantnumberEP/R025754/1en
dc.identifier.grantnumberRF-2022-014en


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