Ruthenium (II)-Catalyzed C–H Functionalization Using the Oxazolidinone Heterocycle as a Weakly Coordinating Directing Group: Experimental and Computational Insights

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dc.cclicenceN/Aen
dc.contributor.authorLeitch, Jamie A.en
dc.contributor.authorWilson, Philippe B.en
dc.contributor.authorMcMullin, Claire L.en
dc.contributor.authorMahon, Mary F.en
dc.contributor.authorBhonoah, Yunasen
dc.contributor.authorWilliams, Ian H.en
dc.date.accessioned2017-01-10T11:48:37Z
dc.date.available2017-01-10T11:48:37Z
dc.date.issued2016-07-14
dc.description.abstractHerein, we report the ruthenium-catalyzed ortho C–H alkenylation of a wide range of N-aryloxazolidinone scaffolds. Alkenylation was achieved with complete monoselectivity with a scope of 27 examples in 2-MeTHF. Yields ranged from 23 to 94%, producing highly decorated oxazolidinone scaffolds. A kinetically relevant C–H cleavage was also observed with a kinetic isotope effect (KIE) of ∼2. Density functional theory calculations provided information about mechanism, detailing the β-hydride elimination as the most energetically challenging step of 13.5 kcal mol–1. In-depth computational kinetic studies also predicted a KIE of 2.17 for C–H cleavage and an intrinsic KIE for the reaction of 2.22, in line with the experimentally observed valueen
dc.exception.reasonArticle is already on University of Bath repository http://opus.bath.ac.uk/51358/en
dc.funderSyngentaen
dc.identifier.citationLeitch, J.A. et al. (2016) Ruthenium(II)-Catalyzed C–H Functionalization Using the Oxazolidinone Heterocycle as a Weakly Coordinating Directing Group: Experimental and Computational Insights. ACS Catalysis, 6 (8), pp. 5520-5529en
dc.identifier.doihttps://doi.org/10.1021/acscatal.6b01370
dc.identifier.urihttp://hdl.handle.net/2086/13154
dc.language.isoen_USen
dc.peerreviewedYesen
dc.projectidN/Aen
dc.publisherACSen
dc.researchinstituteLeicester Institute for Pharmaceutical Innovation - From Molecules to Practice (LIPI)en
dc.subjectC−H activationen
dc.subjectDFTen
dc.subjectheterocyclesen
dc.subjecthomogeneous catalysisen
dc.subjectkinetic isotope effecten
dc.subjectrutheniumen
dc.titleRuthenium (II)-Catalyzed C–H Functionalization Using the Oxazolidinone Heterocycle as a Weakly Coordinating Directing Group: Experimental and Computational Insightsen
dc.typeArticleen

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