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dc.contributor.authorShi, Yiping
dc.contributor.authorKamer, Paul C. J.
dc.contributor.authorCole-Hamilton, David J.
dc.contributor.authorHarvie, Michelle
dc.contributor.authorBaxter, Emma F.
dc.contributor.authorLim, Kate J. C.
dc.contributor.authorPogorzelec, Peter
dc.identifier.citationShi , Y , Kamer , P C J , Cole-Hamilton , D J , Harvie , M , Baxter , E F , Lim , K J C & Pogorzelec , P 2017 , ' A new route to N-aromatic heterocycles from the hydrogenation of diesters in the presence of anilines ' , Chemical Science , vol. 8 , no. 10 , pp. 6911-6917 .
dc.identifier.otherPURE: 250714446
dc.identifier.otherPURE UUID: a9c16670-60c5-4b4e-8539-59621cdc80b8
dc.identifier.otherScopus: 85030111288
dc.identifier.otherWOS: 000411730500022
dc.descriptionThe authors thank the EPSRC for the critical mass grant 'Clean Catalysis for Sustainable Development' (EP/J018139/1), Sasol Technology, UK for a case studentship (Y. S.) and the EPSRC UK National Mass Spectrometry Facility at Swansea University for mass spectrometric analysis.en
dc.description.abstractThe hydrogenation of dicarboxylic acids and their esters in the presence of anilines provides a new synthesis of heterocycles. [Ru(acac)3] and 1,1,1-tris(diphenylphosphinomethyl)ethane (triphos) gave good to excellent yields of the cyclic amines at 220 °C. When aqueous ammonia was used with dimethyl 1,6-hexadienoic acid, ε-caprolactam was obtained in good yield. A side reaction involving alkylation of the amine by methanol was suppressed by using diesters derived from longer chain and branched alcohols. Hydrogenation of optically pure diesters (dimethyl (R)-2-methylbutanedioate and dimethyl (S)-2- methylbutanedioate) with aniline afforded racemic 3-methyl-1-phenylpyrrolidine in 78 % yield.
dc.relation.ispartofChemical Scienceen
dc.rightsCopyright 2017 the authors. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material.en
dc.subjectQD Chemistryen
dc.titleA new route to N-aromatic heterocycles from the hydrogenation of diesters in the presence of anilinesen
dc.typeJournal articleen
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews.School of Chemistryen
dc.contributor.institutionUniversity of St Andrews.EaSTCHEMen
dc.description.statusPeer revieweden

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