Selective introduction of nitrogen into bulk chemicals via homogeneously catalyzed reactions
Date
2024
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Abstract
Nitrogen-containing chemical compounds are used everywhere in our day-to-day lives, from high-performance polymers to pharmaceuticals and crop protection. Despite being produced on very large scale, many of their production lines lack efficiency and have a significant impact on the environment.
Amides are often synthesized by highly activated coupling agents with an inherently low E-factor. Therefore, developing a catalytic reaction that can produce amides directly from bulk chemicals is highly desired. Primary amines are essential intermediates in the chemical industry, and their selective synthesis is challenging due to their reactive properties. Although they are also produced from bulk feedstock, they require many steps when a renewable substrate is used.
This dissertation addresses these challenges by developing and optimizing homogeneous transition metal catalysts. The work is structured into three main parts, each addressing different types of reactions to introduce nitrogen into bulk chemicals:
1. Carbonylative telomerization is a complex chemical reaction that synthesizes amides from simple feedstock molecules, but its high catalyst loading presents a challenge, as well as a limited scope. Both were addressed by optimizing the reaction conditions and adding new dienes and nucleophiles to the reaction portfolio of carbonylative telomerization.
2. Converting fatty esters directly into amines in a one-pot reaction is sought to streamline chemical production, requiring the development of a new catalyst to facilitate the process and improve resource and energy efficiency. Therefore, modified triphos ligands were synthesized and combined with ester amination.
3. The conversion of aldoximes into primary amines, offers a possible alternative to the highly desired hydroamination of alkenes. This is achieved through the combination with hydroformylation, which enables the conversion of alkenes into primary.
These contributions offer new efficient ways of introducing nitrogen into bulk feedstock to synthesize more complex amides and primary amines through homogeneous transition metal catalysts.
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Keywords
Katalyse, Amine, Amide, Phosphine