Selectivity Control in Ruthenium- and Cobalt-Catalysed C–H Activation of Pharmaceuticals

by Yonglin Lai
Doctoral thesis
Date of Examination:2025-08-27
Date of issue:2025-12-17
Advisor:Prof. Dr. Lutz Ackermann
Referee:Prof. Dr. Lutz Ackermann
Referee:Dr. Magnus Johansson
Referee:Prof. Dr. Konrad Koszinowski
Referee:Dr. Daniel Janßen-Müller
Referee:Prof. Dr. Johannes C. L. Walker
Referee:Dr. Holm Frauendorf
Persistent Address: http://dx.doi.org/10.53846/goediss-11587

 

 

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Abstract

English

The construction of C–C bonds is of great significance because C–C bonds are the fundamental linkages and the backbones of pharmaceuticals, agrochemicals, natural products and various materials. Consequently, the chemistry community calls for milder and more sustainable synthetic methodologies for making such bonds, and new strategies to construct previously inaccessible molecules through C–C bond formation. In this thesis, several different transformations to selectively functionalise arenes through new C–C bond formation were investigated, guided by high-throughout experimentation. In each project, late-stage functionalisation was implemented to demonstrate its applicability in medicinal chemistry and drug discovery. In the first project, we developed a redox-neutral, base-free method for the rutheniumcatalysed ortho-C(sp²)−H aminocarbonylation of anthranilamide. The second project explored the possibility of developing a more sustainable and efficient method for the direct alkylation of arenes using earth abundant cobalt catalyst. In the third project, we have developed a strategy for meta-selective C–H methylation and mono-, di-, and trifluoromethylation of arenes, allowing for the rapid access of various C1-substituted compounds from a single parent molecule.
Keywords: C-H Activation; High-throughput Experimentation; Transition-metal Catalysis; Late-stage Functionalisation; Sustainable Chemistry
 
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