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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.identifier177993727
dc.identifier524efb98-9534-4159-b4cb-f95978420840
dc.identifier84930221830
dc.identifier000355314100038
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.otherORCID: /0000-0002-2104-7313/work/36567499
dc.identifier.urihttps://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.format.extent752440
dc.language.isoeng
dc.relation.ispartofAngewandte Chemie International Editionen
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.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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