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Monitoring of Thiol-Ene Coupling by Mass Spectrometry and Ion Mobility Spectrometry

  • The carbon-sulfur bond is frequently occurring in natural products and pharmaceuticals. In a wide range of industrial applications such as polymers and bioorganic functionalization, biomaterials and nanostructured networks formation and microdevice fabrication the targeted construction of C-S bonds is being synthetically important. The synthesis of thioethers is mainly conducted by radical thiol-ene click reactions typically initiated by thermal or UV activation of a radical initiator or direct radical formation via UV irradiation. The reported conversion yields are high after relatively short irradiation times, thus, a fast reaction monitoring is necessary to optimize reaction conditions in terms of total yield and occurrence of undesired by-products. Especially for fast reactions, rapid response is the key feature for online monitoring. The latter gets increasingly important in process analytical approaches for quality assurance and to better control the conversion rate byThe carbon-sulfur bond is frequently occurring in natural products and pharmaceuticals. In a wide range of industrial applications such as polymers and bioorganic functionalization, biomaterials and nanostructured networks formation and microdevice fabrication the targeted construction of C-S bonds is being synthetically important. The synthesis of thioethers is mainly conducted by radical thiol-ene click reactions typically initiated by thermal or UV activation of a radical initiator or direct radical formation via UV irradiation. The reported conversion yields are high after relatively short irradiation times, thus, a fast reaction monitoring is necessary to optimize reaction conditions in terms of total yield and occurrence of undesired by-products. Especially for fast reactions, rapid response is the key feature for online monitoring. The latter gets increasingly important in process analytical approaches for quality assurance and to better control the conversion rate by feedback control. For a headspace analysis, gas detection methods like ion mobility spectrometry (IMS) and mass spectrometry (MS) are especially suitable to this aim since they provide response times in the ms - s range. Moreover, as complementary methods they provide comprehensive information about the molecule and it's structure. The aim of the work is to qualitatively interrogate the sample composition of a photocatalytically initiated thiol-ene coupling in real time. This contribution presents primary results of direct analysis of the photoinitiated synthesis of methyl 2-((tert-butoxycarbonyl)amino)-3-((3-hydroxypropyl)thio) propanoate by IMS and MS utilizing different ionization sources. The thiol-ene reaction is performed between N-Boc-cysteine methyl ester and allyl alcohol utilizing Ru(bpz)3(PF6)2 catalyst as a photoinitiator and p-toluidine as a redox mediator, irradiated at 450 nm according to the procedure presented in [2]. The obtained results were validated by NMR analysis unambiguously indicating the formation of the newly formed C-S bond and additionally providing total reaction yield calibration curves for a quantitative analysis.zeige mehrzeige weniger

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Metadaten
Autor*innen:Aleksandra Michalik-Onichimowska
Koautor*innen:Jens Riedel, Ulrich Panne
Dokumenttyp:Posterpräsentation
Veröffentlichungsform:Präsentation
Sprache:Deutsch
Titel des übergeordneten Werkes (Deutsch):ESCRE 2015
Jahr der Erstveröffentlichung:2015
Veranstaltung:ESCRE 2015
Veranstaltungsort:München
Beginndatum der Veranstaltung:2015-10-27
Enddatum der Veranstaltung:2015-10-30
Verfügbarkeit des Dokuments:Weder Datei noch physisches Exemplar vorhanden ("No Access")
Datum der Freischaltung:20.02.2016
Referierte Publikation:Nein
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