Light-induced palladium-catalyzed Buchwald Hartwig aminationOštir, Andraž (Avtor) Krajnc, Peter (Mentor) Goossen, Lucas J. (Komentor) Buchwald-Hartwig aminationphotochemistrypalladiumroom temperatureammonium saltThe goal of this master’s thesis was to investigate the use of light to enable the acceleration of the Buchwald-Hartwig amination of deactivated aryl chlorides with an ammonium source using a newly developed and optimized state-of-the-art catalyst system. A photoreactor was designed, modelled, and constructed to allow for a reproducible reaction setup under controlled conditions. The optimal light source and reaction conditions were investigated using a model reaction. Conversion of the starting material, product yield and potential byproducts were quantified by gas chromatography (GC) analysis and confirmed by mass spectroscopy (GC/MS). The use of light (3 W 447 nm) enabled the accelerated conversion of aryl chlorides towards the amination products even at room temperature in 2 hours, which is a remarkable improvement upon the previously reported state-of-the-art. Under optimized conditions, the highest yield (88 %) was achieved using a catalyst complex formed from β-methyl naphthyl (β-MeNAP) palladium bromide and the sterically demanding ligand AdBrettPhos. The structure of the complex crystal was elucidated using X-ray crystallography after the crystallization of the catalyst species.[A. Oštir]20232023-09-15 02:27:13Magistrsko delo/naloga85857sl