Studies Toward Selenium-pi-Acid Catalyzed Oxidative Functionalizations of Olefinic and Acetylenic Multiple Bonds

by Katharina Rode
Doctoral thesis
Date of Examination:2020-08-19
Date of issue:2020-09-24
Advisor:Prof. Dr. Alexander Breder
Referee:Prof. Dr. Alexander Breder
Referee:Prof. Dr. Lutz Ackermann
Referee:Dr. Holm Frauendorf
Referee:Prof. Dr. Inke Siewert
Referee:Prof. Dr. Dietmar Stalke
Referee:Prof. Dr. Konrad Koszinowski
Persistent Address: http://dx.doi.org/10.53846/goediss-8213

 

 

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Abstract

English

The focus of this thesis was the oxidative functionalization of alkenes via selenium-pi-acid catalysis. In the realm of dual photoredox/selenium-pi-acid catalysis, the known methodology was expanded to the use of alcohols as endogenous nucleophiles in intra- and intermolecular etherification reactions. Furthermore, the scope of cognate lactonization and phosphatation reactions was determined. During the investigation of alkynes as alternative substrates for selenium-catalyzed reactions, the formation of allenylamides was developed and based on control experiments, a mechanism for the transformation was proposed. Finally, the use of nitrogen nucleophiles was examined and chiral binaphthyl-based diselenide catalysts were synthesized.
Keywords: selenium; photoredox catalysis; alkene functionalization; alkyne functionalization; allenes
 
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