Synthesis of Pyrrolo[1,2-c]pyrimidine-1-ylidenes: Coordination Chemistry and Application as Ancillary Ligands for Metal Catalysis

by Daniel Rösch
Doctoral thesis
Date of Examination:2025-01-16
Date of issue:2025-03-20
Advisor:Prof. Dr. Manuel Alcarazo
Referee:Prof. Dr. Manuel Alcarazo
Referee:Prof. Dr. Johannes C. L. Walker
Referee:Prof. Dr. Christian Sindlinger
Referee:Prof. Dr. Dietmar Stalke
Referee:Prof. Dr. Anna Jun.-Krawczuk
Referee:Prof. Dr. Daniel Jun.-Obenchain
Referee:Dr. Michael John
Persistent Address: http://dx.doi.org/10.53846/goediss-11163

 

 

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Abstract

English

N-heterocyclic carbenes (NHCs) represent an important class of ancillary ligands for transition metal catalysis due to their strong binding character and generally simple syntheses procedures. One important feature of these ligands is their facile electronic tunability by rational design. Furthermore, the steric properties can be tuned in a similar manner. Despite extensive research activity in the field of carbenes for more than 30 years, the system of pyrimidine has been scarcely discussed as a base for carbenes. Targeting one of these systems, this work explores the properties of the bicyclic pyrrolo[1,2-c]pyrimidine-1-ylidene. In this thesis, the synthesis of different substitution patterns of the desired scaffold have been developed. The free carbene was isolated and corresponding metal complexes were synthesized. Furthermore, the structures of said complexes were studied in depth and their catalytic utilities were explored. Furthermore, a big component of this work is the electronic characterization of the novel system via different analytic methods and comparison to literature known systems. The studies indicated a strong σ donor character as well as π acceptor character of the regarded framework and a particularly high steric crowdedness around the metal center.
Keywords: Carbene; NHC; Catalysis
 
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