S-Substituted Dibenzothiophenium Triflates: Synthesis, Structure and Reactivity

by Kevin Kafuta
Doctoral thesis
Date of Examination:2021-04-08
Date of issue:2021-04-23
Advisor:Prof. Dr. Manuel Alcarazo
Referee:Prof. Dr. Dietmar Stalke
Referee:Prof. Dr. Ulf Diederichsen
Referee:Dr. Matthias Otte
Referee:Prof. Dr. Johannes C. L. Walker
Referee:Dr. Christian Sindlinger
Persistent Address: http://dx.doi.org/10.53846/goediss-8558

 

 

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Abstract

English

The content of this thesis focused on the general syntheses and applications S-substituted alkynyl-, alkenyl- and aryldibenzothiophenium triflates. Addition reactions have been performed from S-alkynyldibenzothiophenium triflates towards vinyl substituted ones. With these in hand, their abilities as potential Michael-acceptors and in photocatalysis were tested. Deprotonated acetylenes delivered diynes by electrophilic alkynylation with S-alkynyldibenzothiophenium triflates. Lastly, a family of S-aryldibenzothiophenium triflates has been synthetized. Postsynthetic modifications including ipso aminations as well as chemoselective suzuki couplings in the presence of common coupling partners such as iodides and triflates have been performed.
Keywords: Sulfonium Salts; Photocatalysis; Palladium Catalysis; Umpolung; Transfer Reagents; Michael Reactions; Diyne Formation
 
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