Synthesis of Novel Sulfur(VI) Reagents and the Regioselective Functionalization of Helicenes by Hypervalent Reagents

by Christian Böhmer
Doctoral thesis
Date of Examination:2024-06-04
Date of issue:2024-06-28
Advisor:Prof. Dr. Manuel Alcarazo
Referee:Prof. Dr. Manuel Alcarazo
Referee:Prof. Dr. Dietmar Stalke
Referee:Prof. Dr. Johannes C. L. Walker
Referee:Prof. Dr. Anna Krawczuk
Referee:Dr. Daniel Janßen-Müller
Referee:Prof. Dr. Konrad Koszinowski
Persistent Address: http://dx.doi.org/10.53846/goediss-10578

 

 

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Abstract

English

The synthesis of novel sulfur(VI) reagents was investigated. For this purpose different sulfurane oxides were synthesized. The functionalization of these compounds was unsuccessful due to decomposition or inertness of the compounds. The related alkoxysulfonium salts could be synthesized, but the compounds proved to be prone to undesired reactivity. A synthesis of sulfoxonium salts by oxidation of the corresponding sulfonium salts was developed. These compounds proved more reactive towards reduction and reaction with nucleophiles and less reactive towards transition metals than their sulfonium counterparts. A comparison of the molecular structures of sulfonium and sulfoxonium salts displayed notable differences, especially with regards to chalcogen bonding. The functionalization of helicenes was also investigated. The functionalization of these compounds via the corresponding sulfonium salts was plagued by undesired side reactions. Instead a highly regioselective direct arylation using iodonium salts was developed and applied to the functionalization of complex helicenes.
Keywords: sulfoxonium; sulfonium; sulfurane; sulfur(VI); helicene; C–H functionalzation
 
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