Synthesis of cyclic alpha-diazo-beta-keto sulfoxides in batch and continuous flow

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dc.contributor.authorMcCaw, Patrick G.
dc.contributor.authorBuckley, Naomi M.
dc.contributor.authorEccles, Kevin S.
dc.contributor.authorLawrence, Simon E.
dc.contributor.authorMaguire, Anita R.
dc.contributor.authorCollins, Stuart G.
dc.contributor.funderScience Foundation Irelanden
dc.contributor.funderIrish Research Council
dc.date.accessioned2017-03-21T16:09:04Z
dc.date.available2017-03-21T16:09:04Z
dc.date.issued2017-03-08
dc.date.updated2017-03-21T15:56:05Z
dc.description.abstractDiazo transfer to beta–keto sulfoxides to form stable isolable alpha-diazo-beta-keto sulfoxides has been achieved for the first time. Both monocyclic and benzofused ketone derived beta-keto sulfoxides were successfully explored as substrates for diazo transfer. Use of continuous flow leads to isolation of the desired compounds in enhanced yields relative to standard batch conditions, with short reaction times, increased safety profile and potential to scale up.en
dc.description.sponsorshipIrish Research Council (Project ID GOIPG/2013/244); Science Foundation Ireland (grant: SFI SSPC2 12/RC/2275)en
dc.description.statusPeer revieweden
dc.description.versionAccepted Versionen
dc.format.mimetypeapplication/pdfen
dc.identifier.citationMcCaw, P. G., Buckley, N. M., Eccles, K. S., Lawrence, S. E., Maguire, A. R. and Collins, S. G. (2017) 'Synthesis of cyclic alpha-diazo-beta-keto sulfoxides in batch and continuous flow', Journal of Organic Chemistry, 82(7), pp. 3666-3679. doi:10.1021/acs.joc.7b00172en
dc.identifier.doi10.1021/acs.joc.7b00172
dc.identifier.endpage3679
dc.identifier.issn0022-3263
dc.identifier.issued7
dc.identifier.journaltitleThe Journal of Organic Chemistryen
dc.identifier.startpage3666
dc.identifier.urihttps://hdl.handle.net/10468/3795
dc.identifier.volume82
dc.language.isoenen
dc.publisherAmerican Chemical Societyen
dc.rightsThis document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://pubs.acs.org/doi/abs/10.1021/acs.joc.7b00172en
dc.subjectDiazo transferen
dc.subjectContinuous flowen
dc.subjectAmberlyst A21en
dc.subjectα-diazo-β-keto-sulfoxideen
dc.titleSynthesis of cyclic alpha-diazo-beta-keto sulfoxides in batch and continuous flowen
dc.typeArticle (peer-reviewed)en
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