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

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dc.contributor.author Deadman, Benjamin J.
dc.contributor.author O'Mahony, Rosella M.
dc.contributor.author Lynch, Denis
dc.contributor.author Crowley, Daniel C.
dc.contributor.author Collins, Stuart G.
dc.contributor.author Maguire, Anita R.
dc.date.accessioned 2020-08-31T13:24:37Z
dc.date.available 2020-08-31T13:24:37Z
dc.date.issued 2016-03-01
dc.identifier.citation Deadman, 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/c6ob00246c en
dc.identifier.volume 14 en
dc.identifier.startpage 3423 en
dc.identifier.endpage 3431 en
dc.identifier.issn 1477-0520
dc.identifier.uri http://hdl.handle.net/10468/10418
dc.identifier.doi 10.1039/c6ob00246c en
dc.description.abstract Heat 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.format.mimetype application/pdf en
dc.language.iso en en
dc.publisher Royal Society of Chemistry en
dc.relation.uri https://pubs.rsc.org/en/content/articlelanding/2016/OB/C6OB00246C
dc.rights © The Royal Society of Chemistry 2016 en
dc.subject Continuous flow synthesis en
dc.subject C-H insertion en
dc.subject Alpha-diazocarbonyl compounds en
dc.subject Hetero-Wolff rearrangement en
dc.subject Beta-oxo sulfoxides en
dc.subject Organic synthesis en
dc.subject Carbene insertion en
dc.title Taming tosyl azide: the development of a scalable continuous diazo transfer process en
dc.type Article (peer-reviewed) en
dc.internal.authorcontactother Anita Maguire, Vice President For Research, University College Cork, Cork, Ireland. +353-21-490-3000 Email: a.maguire@ucc.ie en
dc.internal.availability Full text available en
dc.date.updated 2020-08-24T14:33:43Z
dc.description.version Accepted Version en
dc.internal.rssid 372342827
dc.internal.wokid 000372795900011
dc.contributor.funder Science Foundation Ireland en
dc.description.status Peer reviewed en
dc.identifier.journaltitle Organic and Biomolecular Chemistry en
dc.internal.copyrightchecked Yes
dc.internal.licenseacceptance Yes en
dc.internal.IRISemailaddress a.maguire@ucc.ie en
dc.internal.IRISemailaddress denis.lynch@ucc.ie en
dc.relation.project info:eu-repo/grantAgreement/SFI/SFI Research Centres/12/RC/2275/IE/Synthesis and Solid State Pharmaceutical Centre (SSPC)/ en
dc.identifier.eissn 1477-0539


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