Enabling Novel Fluoroalkylation via Sulfonium Salt Transfer Reagents

von Zeyu Feng
Dissertation
Datum der mündl. Prüfung:2024-07-16
Erschienen:2024-08-26
Betreuer:Prof. Dr. Manuel Alcarazo
Gutachter:Prof. Dr. Manuel Alcarazo
Gutachter:Prof. Dr. Konrad Koszinowski
Zum Verlinken/Zitieren: http://dx.doi.org/10.53846/goediss-10696

 

 

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Zusammenfassung

Englisch

Over the past four decades, sulfonium salt-based transfer reagents have evolved into widely recognized tools for fluoroalkylation in the synthetic chemistry community. These reagents have enabled the incorporation of various small fluorinated alkyl moieties into complex structures. However, their application has predominantly been limited to fluoromethyl groups, such as CF3, CF2H, and CFH2. While these groups are crucial in drug discovery and the agrochemical industry, there is a growing demand for new types of fluorinated alkyl fragments that could exhibit novel and beneficial effects beyond those offered by existing fluorinated groups. In this dissertation, we will present the design, synthesis, and application of a series of new sulfonium salt transfer reagents. These reagents are specifically developed to introduce unique fluorinated alkyl motifs, including the 1,2,2-trifluoroethylene tether, pentafluorocyclopropyl, and 2,3-bis(trifluoromethyl)cyclopropyl groups. These motifs have not previously been incorporated into structures of medicinal interest, likely due to the lack of feasible methods for their introduction. Our development of these novel reagents aims to provide a platform for further exploration of these unprecedented functional groups.
Keywords: sulfonium salts; fluorination; radical chemistry; fluoroalkylation; photocatalysis
 
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