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Novel Cationic Sulfur Reagents and their Application in Electrophilic Group-Transfer Reactions

dc.contributor.advisorAlcarazo, Manuel Prof. Dr.
dc.contributor.authorAveresch, Kai Florian Gustav
dc.date.accessioned2020-06-08T09:20:40Z
dc.date.available2020-06-08T09:20:40Z
dc.date.issued2020-06-08
dc.identifier.urihttp://hdl.handle.net/21.11130/00-1735-0000-0005-13C9-3
dc.identifier.urihttp://dx.doi.org/10.53846/goediss-8012
dc.language.isodeude
dc.publisherNiedersächsische Staats- und Universitätsbibliothek Göttingende
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/
dc.subject.ddc540de
dc.titleNovel Cationic Sulfur Reagents and their Application in Electrophilic Group-Transfer Reactionsde
dc.typedoctoralThesisde
dc.contributor.refereeAlcarazo, Manuel Prof. Dr.
dc.date.examination2019-12-18
dc.description.abstractengThe two major research achievements of this work are the development of novel sulfur-based electrophilic transfer reagents based on pyridinium, as well as the extension of the reactivity of already established imidazolium based electrophilic reagents to transition metal catalysis. Both projects share the rationale of electron deficient, nitrogen heterocycles used as backbones, for the polarization of triple bonds to enable new reaction pathways. The synthesis of alkynylthiopyridinium salts, was developed and their reaction with nucleophiles was thioacylation in most cases. The mode of reactivity of these reagents is reminiscent of that of thioketenes. This gave access to dithioesters, thioamides and thionoesters in good to excellent yields under remarkably mild conditions. While for pyridinium based reagents a scope of its reactivity with S-, N- and O-nucleophiles under metal free conditions was investigated, for imidazolium based transfer reagents, a rhodium catalyzed C-H-functionalization protocol with weakly coordinating benzamides was established. A sequence consisting of electrophilic alkynylation of N-methylbenzamides, followed by annulation and finally, hydrolysis of isochromene iminium salts, gave isocoumarins as final products.de
dc.contributor.coRefereeMeyer, Franc Prof. Dr.
dc.contributor.thirdRefereeKoszinowski, Konrad Prof. Dr.
dc.contributor.thirdRefereeStalke, Dietmar Prof. Dr.
dc.contributor.thirdRefereeSindlinger, Christian Dr.
dc.subject.engelectrophilic alkynylationde
dc.subject.engUmpolungde
dc.subject.engalkynylthioimidazolium saltsde
dc.subject.engalkynylthiopyridinium saltsde
dc.subject.engdithioestersde
dc.subject.engpyridinium saltsde
dc.subject.engsulfuranesde
dc.subject.engthioamidesde
dc.subject.engthioketenesde
dc.subject.engreagentsde
dc.subject.engC-H activationde
dc.subject.engrhodium catalysisde
dc.subject.engisocoumarinsde
dc.identifier.urnurn:nbn:de:gbv:7-21.11130/00-1735-0000-0005-13C9-3-9
dc.affiliation.instituteFakultät für Chemiede
dc.subject.gokfullChemie  (PPN62138352X)de
dc.identifier.ppn1700195166


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