Enabling Novel Fluoroalkylation via Sulfonium Salt Transfer Reagents

by Zeyu Feng
Doctoral thesis
Date of Examination:2024-07-16
Date of issue:2024-08-26
Advisor:Prof. Dr. Manuel Alcarazo
Referee:Prof. Dr. Manuel Alcarazo
Referee:Prof. Dr. Konrad Koszinowski
Persistent Address: http://dx.doi.org/10.53846/goediss-10696

 

 

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Abstract

English

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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