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Rate and equilibrium constants for the addition of N-heterocyclic carbenes into benzaldehydes : a remarkable 2-substituent effect

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dc.contributor.authorCollett, Christopher John
dc.contributor.authorMassey, Richard S
dc.contributor.authorTaylor, James Edward
dc.contributor.authorMaguire, Oliver R
dc.contributor.authorO'Donoghue, AnnMarie C
dc.contributor.authorSmith, Andrewv D.
dc.date.accessioned2015-07-30T13:40:01Z
dc.date.available2015-07-30T13:40:01Z
dc.date.issued2015-05-27
dc.identifier.citationCollett , C J , Massey , R S , Taylor , J E , Maguire , O R , O'Donoghue , A C & Smith , A D 2015 , ' Rate and equilibrium constants for the addition of N-heterocyclic carbenes into benzaldehydes : a remarkable 2-substituent effect ' , Angewandte Chemie International Edition , vol. 54 , no. 23 , pp. 6887-6892 . https://doi.org/10.1002/anie.201501840en
dc.identifier.issn1433-7851
dc.identifier.otherPURE: 177993727
dc.identifier.otherPURE UUID: 524efb98-9534-4159-b4cb-f95978420840
dc.identifier.otherScopus: 84930221830
dc.identifier.otherORCID: /0000-0002-2104-7313/work/36567499
dc.identifier.otherWOS: 000355314100038
dc.identifier.urihttp://hdl.handle.net/10023/7082
dc.descriptionWe thank the Royal Society for a University Research Fellowship (ADS), the EPSRC (CJC and RM) grant number EP/G013268/1 and the European Research Council under the European Union's Seventh Framework Programme (FP7/2007-2013) ERC grant agreement no 279850 (JET). We also thank the EPSRC UK National Mass Spectrometry Facility at Swansea University.en
dc.description.abstractRate and equilibrium constants for the reaction between N-aryl triazolium NHC precatalysts and substituted benzaldehyde derivatives to form 3-(hydroxybenzyl)azolium adducts under both catalytic and stoichiometric conditions have been measured. Kinetic analysis and reaction profile fitting of both the forward and reverse reactions, plus onwards reaction to the Breslow intermediate, demonstrate the remarkable effect of the benzaldehyde 2-substituent in these reactions and provide insight into the chemoselectivity of cross-benzoin reactions.
dc.language.isoeng
dc.relation.ispartofAngewandte Chemie International Editionen
dc.rightsCopyright 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.en
dc.subjectN-heterocyclic carbenesen
dc.subjectOrganocatalysisen
dc.subjectMechanistic studiesen
dc.subjectKineticsen
dc.subject2-substituent effecten
dc.subjectQD Chemistryen
dc.subjectNDASen
dc.subjectBDCen
dc.subject.lccQDen
dc.titleRate and equilibrium constants for the addition of N-heterocyclic carbenes into benzaldehydes : a remarkable 2-substituent effecten
dc.typeJournal articleen
dc.contributor.sponsorEuropean Commissionen
dc.contributor.sponsorEPSRCen
dc.contributor.sponsorThe Royal Societyen
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.contributor.institutionUniversity of St Andrews. EaSTCHEMen
dc.contributor.institutionUniversity of St Andrews. Biomedical Sciences Research Complexen
dc.identifier.doihttps://doi.org/10.1002/anie.201501840
dc.description.statusPeer revieweden
dc.identifier.grantnumberN/Aen
dc.identifier.grantnumberEP/G013268/1en
dc.identifier.grantnumberUF090013en


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