Taming tosyl azide: the development of a scalable continuous diazo transfer process

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dc.contributor.authorDeadman, Benjamin J.
dc.contributor.authorO'Mahony, Rosella M.
dc.contributor.authorLynch, Denis
dc.contributor.authorCrowley, Daniel C.
dc.contributor.authorCollins, Stuart G.
dc.contributor.authorMaguire, Anita R.
dc.contributor.funderScience Foundation Irelanden
dc.date.accessioned2020-08-31T13:24:37Z
dc.date.available2020-08-31T13:24:37Z
dc.date.issued2016-03-01
dc.date.updated2020-08-24T14:33:43Z
dc.description.abstractHeat and shock sensitive tosyl azide was generated and used on demand in a telescoped diazo transfer process. Small quantities of tosyl azide were accessed in a 'one pot' batch procedure using shelf stable, readily available reagents. For large scale diazo transfer reactions tosyl azide was generated and used in a telescoped flow process, to mitigate the risks associated with handling potentially explosive reagents on scale. The in situ formed tosyl azide was used to rapidly perform diazo transfer to a range of acceptors, including beta-ketoesters, beta-ketoamides, malonate esters and beta-ketosulfones. An effective in-line quench of sulfonyl azides was also developed, whereby a sacrificial acceptor molecule ensured complete consumption of any residual hazardous diazo transfer reagent. The telescoped diazo transfer process with in-line quenching was used to safely prepare over 21 g of an alpha-diazocarbonyl in > 98% purity without any column chromatography.en
dc.description.statusPeer revieweden
dc.description.versionAccepted Versionen
dc.format.mimetypeapplication/pdfen
dc.identifier.citationDeadman, B. J., O'Mahony, R. M., Lynch, D., Crowley, D. C., Collins, S. G. and Maguire, A. R. (2016) 'Taming tosyl azide: the development of a scalable continuous diazo transfer process', Organic & Biomolecular Chemistry, 14(13), pp. 3423-3431. doi: 10.1039/c6ob00246cen
dc.identifier.doi10.1039/c6ob00246cen
dc.identifier.eissn1477-0539
dc.identifier.endpage3431en
dc.identifier.issn1477-0520
dc.identifier.journaltitleOrganic and Biomolecular Chemistryen
dc.identifier.startpage3423en
dc.identifier.urihttps://hdl.handle.net/10468/10418
dc.identifier.volume14en
dc.language.isoenen
dc.publisherRoyal Society of Chemistryen
dc.relation.projectinfo:eu-repo/grantAgreement/SFI/SFI Research Centres/12/RC/2275/IE/Synthesis and Solid State Pharmaceutical Centre (SSPC)/en
dc.relation.urihttps://pubs.rsc.org/en/content/articlelanding/2016/OB/C6OB00246C
dc.rights© The Royal Society of Chemistry 2016en
dc.subjectContinuous flow synthesisen
dc.subjectC-H insertionen
dc.subjectAlpha-diazocarbonyl compoundsen
dc.subjectHetero-Wolff rearrangementen
dc.subjectBeta-oxo sulfoxidesen
dc.subjectOrganic synthesisen
dc.subjectCarbene insertionen
dc.titleTaming tosyl azide: the development of a scalable continuous diazo transfer processen
dc.typeArticle (peer-reviewed)en
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