Improving Palladium Catalyzed C–H Activation Methodologies Towards Industrial Applicability

With the common goal of addressing C–H activation challenges in order to accelerate its use in industrial applications, in the dissertation presented herein, three projects will be presented and discussed. In the first chapter, we decided to tackle the concerns behind high catalyst loadings and catalyst reactivity. Inspired by the concept of hemilability, and in an attempt to enhance the steric properties and reactivity of our dual ligand catalyst, we developed a series of hemilabile ligands. In the second chapter, following the principle of sustainable development, we addressed the replacement of silver with a more environmentally benign oxidant. The advantages of this protocol would be improved atom economy, less generated waste and lower cost, i.e. attractive selling points for potential industrial applicability. Taking inspiration from the Wacker Process, promising results came from the combination between Copper, as co-catalyst, and molecular oxygen as terminal oxidant. In the third chapter, we focused on how to support industry in the synthesis of complex molecules. Since during drug discovery, high throughput screening campaigns are done to spot molecules of interest, building libraries of compounds in a fast and efficient way is of utmost importance. Hence, we developed and reported a sterically controlled C(sp2)–H carboxylation and formylation of arenes, as a complementary method to electrophilic aromatic substitution approaches. We aspire that the chapters presented will encourage further development and improvement of C–H activation methodologies, for practical deployment in industrial settings.

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