Synthesis and reactivity of α-diazo-β-keto sulfonamides

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dc.check.date2025-06-19en
dc.check.infoAccess to this article is restricted until 12 months after publication by request of the publisheren
dc.contributor.authorMaguire, Anita R.en
dc.contributor.authorJudge, Evanen
dc.contributor.authorO'Shaughnessy, Keith A.en
dc.contributor.authorLawrence, Simon E.en
dc.contributor.authorCollins, Stuart G.en
dc.contributor.funderScience Foundation Irelanden
dc.contributor.funderIrish Research Councilen
dc.contributor.funderHigher Education Authorityen
dc.contributor.funderSynthesis and Solid State Pharmaceutical Centreen
dc.contributor.funderEuropean Regional Development Funden
dc.date.accessioned2024-07-15T09:25:16Z
dc.date.available2024-07-15T09:25:16Z
dc.date.issued2024-06-19en
dc.description.abstractCopper mediated reactions of α-diazo-β-keto sulfonamides 1 leads to a range of products including the alkyne sulfonamides 5, the enamines 6, and the α-halosulfonamides 7 and 11 with no evidence for intramolecular C–H insertion in any of the reactions, in contrast to the reactivity of the comparable α-diazo-β-keto sulfones. Use of copper(II) triflate (5 mol%) led to isolation of a series of alkyne sulfonamides 5 (up to 12%) and enamines 6 (up to 64%). Use of copper(II) chloride (5 mol%) formed, in addition, the α-halosulfonamides 7; use of stoichiometric amounts of copper(II) chloride/bromide enables facile halogenation of the β-keto sulfonamide to form the α-halosulfonamides 7 and 11 (up to 63%).en
dc.description.sponsorshipIrish Research Council (GOIPG/2020/369); Science Foundation Ireland (SFI SSPC3 Pharm5 12/RC/2275_2; 05/PICA/B802/EC07)en
dc.description.statusPeer revieweden
dc.description.versionAccepted Versionen
dc.format.mimetypeapplication/pdfen
dc.identifier.citationMaguire, A. R., Judge, E., O'Shaughnessy, K. A., Lawrence, S. E. and Collins, S. G. (2024) 'Synthesis and reactivity of α-diazo-β-keto sulfonamides', Synthesis, 56(24), pp. 3752-3768. https://doi.org/10.1055/a-2348-5631en
dc.identifier.doihttps://doi.org/10.1055/a-2348-5631en
dc.identifier.eissn1437-210Xen
dc.identifier.endpage3768
dc.identifier.issn0039-7881en
dc.identifier.issued24
dc.identifier.journaltitleSynthesisen
dc.identifier.startpage3752
dc.identifier.urihttps://hdl.handle.net/10468/16122
dc.identifier.volume56
dc.language.isoenen
dc.publisherGeorg Thieme Verlag KGen
dc.relation.projectinfo:eu-repo/grantAgreement/SFI/SFI Equipment Call/05/PICA/B802/EC07/IE/Single Crystal X-Ray Diffractometer/en
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.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.projectinfo:eu-repo/grantAgreement/SFI/SFI Research Infrastructure Programme/21/RI/9705/IE/Fast reaction kinetics in NMR Spectroscopy - FaNS/en
dc.relation.project5/PICA/B802/EC07en
dc.rights© 2024, Thieme. All rights reserved.en
dc.subjectα-diazo-β-keto sulfonamidesen
dc.subjectAlkyne sulfonamideen
dc.subjectEnamineen
dc.subjectα-halosulfonamideen
dc.titleSynthesis and reactivity of α-diazo-β-keto sulfonamidesen
dc.typeArticle (peer-reviewed)en
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