Telescoped diazo transfer and rhodium-catalysed S-H insertion in continuous flow

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dc.contributor.authorKearney, Aoife M.
dc.contributor.authorLynch, Dennis
dc.contributor.authorCollins, Stuart G.
dc.contributor.authorMaguire, Anita R.
dc.contributor.funderIrish Research Councilen
dc.contributor.funderScience Foundation Irelanden
dc.contributor.funderEuropean Regional Development Funden
dc.date.accessioned2022-01-19T13:25:55Z
dc.date.available2022-01-19T13:25:55Z
dc.date.issued2021-09-29
dc.date.updated2022-01-19T13:15:54Z
dc.description.abstractRhodium-catalysed S–H insertion of α-diazo-γ-butyrolactams has been successfully telescoped using continuous processing with in situ generated triflyl azide in flow and deacylative diazo transfer, incorporating real-time reaction monitoring of the final process outflow by IR spectroscopy. Significantly, the α-diazo-γ-butyrolactam reaction stream was sufficiently pure to progress to the rhodium-catalysed S–H insertion step without detrimental impact on the rhodium catalyst or the reaction efficiency.en
dc.description.sponsorshipIrish Research Council (IRC GOIPG/2018/112)en
dc.description.statusPeer revieweden
dc.description.versionPublished Versionen
dc.format.mimetypeapplication/pdfen
dc.identifier.articleid153438en
dc.identifier.citationKearney, A., Lynch, D., Collins, S. and Maguire, A. (2021) ‘Telescoped diazo transfer and rhodium-catalysed S–H insertion in continuous flow’, Tetrahedron Letters, 83, 153438 (4 pp). doi: 10.1016/j.tetlet.2021.153438en
dc.identifier.doi10.1016/j.tetlet.2021.153438en
dc.identifier.endpage4en
dc.identifier.issn0040-4039
dc.identifier.journaltitleTetrahedron Lettersen
dc.identifier.startpage1en
dc.identifier.urihttps://hdl.handle.net/10468/12424
dc.identifier.volume83en
dc.language.isoenen
dc.publisherElsevieren
dc.relation.projectinfo:eu-repo/grantAgreement/SFI/SFI Research Centres/12/RC/2275/IE/Synthesis and Solid State Pharmaceutical Centre (SSPC)/en
dc.relation.projectinfo:eu-repo/grantAgreement/SFI/SFI Research Infrastructure Programme/15/RI/3221/IE/Process Flow Spectroscopy (ProSpect); Advanced Reaction Understanding using Flow Nuclear Magnetic Resonance (NMR) and Infrared (IR) Spectroscopies, with On-Line Ultra-Performance Liquid Chromatography (UPLC) and Mass Spectrometry (MS)/en
dc.relation.urihttps://www.sciencedirect.com/science/article/pii/S0040403921007140
dc.rights© 2021 The Author(s). Published by Elsevier Ltd. This is an open access article under the CC BY licenseen
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/en
dc.subjectDiazo transferen
dc.subjectTelescoped continuous processesen
dc.subjectRhodium carboxylate catalysten
dc.subjectTaming hazardous chemistryen
dc.subjectTrifluoromethanesulfonyl azideen
dc.subjectAlpha-sulfonylen
dc.subjectTriflyl azideen
dc.subjectSafeen
dc.subjectGenerationen
dc.subjectEfficienten
dc.subjectReagenten
dc.subjectα-Diazolactamsen
dc.subjectS–H insertionen
dc.titleTelescoped diazo transfer and rhodium-catalysed S-H insertion in continuous flowen
dc.typeArticle (peer-reviewed)en
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