Sustainable Syntheses of Substituted Heterocycles through Ruthenium- and Palladium-Catalyzed Direct C−H Bond Functionalizations

by Christoph Frank Kornhaaß
Doctoral thesis
Date of Examination:2014-06-20
Date of issue:2014-10-22
Advisor:Prof. Dr. Lutz Ackermann
Referee:Prof. Dr. Lutz Ackermann
Referee:Prof. Dr. Ulf Diederichsen
Persistent Address: http://dx.doi.org/10.53846/goediss-4750

 

 

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Abstract

English

The research presented within this thesis is focused on the development of new synthetic methods for the construction of heterocyclic frameworks through ruthenium- and palladium-catalyzed direct C–H bond functionalizations. A new palladium-catalyzed direct alkynylation of oxazoles and thiazoles was elaborated using gem-dichloroalkenes as electrophiles. Furthermore a novel isoquinoline-synthesis was developed, based on an alkyne-annulation via ruthenium-catalyzed direct C–H bond functionalizations of oximes. A similar approach was used for a copper-free aerobic alkyne-annulation through ruthenium-catalyzed direct C–H bond functionalizations of benzoic acids resulting in the formation of isocoumarins.
Keywords: Catalysis; Direct C-H Functionalization; Ruthenium-Catalyzed Annulations; Heterocycles; Palladium-Catalyzed Alkynylations; Sustainable Synthesis
 
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