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Light-induced palladium-catalyzed Buchwald Hartwig amination : master's thesis
Andraž Oštir, 2023, magistrsko delo

Opis: The 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.
Ključne besede: Buchwald-Hartwig amination, photochemistry, palladium, room temperature, ammonium salt
Objavljeno v DKUM: 03.10.2023; Ogledov: 537; Prenosov: 50
.pdf Celotno besedilo (3,76 MB)

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