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Development of novel synthetic methodologies using boron Lewis acids

Guerzoni, Michael 2024. Development of novel synthetic methodologies using boron Lewis acids. PhD Thesis, Cardiff University.
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Abstract

The work described in this thesis concerns the use of Lewis acidic boron-based catalysts as a tool for the development of novel reaction methodologies, with a major focus on the use of B(C6F5)3. Chapter 1 serves as a general introduction to the field of catalysis, and the impact that Lewis acids have on it. Paramount for the utilisation of Lewis acids is knowing their relative strength, hence a discussion of the available methods for assessing the Lewis acidity is also included. Chapter 2 discusses the studies undertaken for the development of a N-functionalisation protocol of indoles using isocyanates. After a topic-related introduction, the research work will be presented. Crucially, it has been shown that the commercially available BCl3 outperforms B(C6F5)3. Chapter 3 highlights the ability of B(C6F5)3 to catalyse either a [3+2] dipolar cycloaddition of vinyl diazo esters or Mukaiyama-Mannich addition of silyl enol diazo esters by activating nitrones. Hence, after another topic-related introduction, a discussion regarding the optimisation studies, substrate scope and further functionalisation of the products will be presented. Chapter 4 builds up from the knowledge developed in Chapter 3 to establish a nitro-Mannich reaction between silyl nitronates and nitrones, again catalysed by B(C6F5)3. After a final topic-related introduction, a discussion of the reaction optimisation, scope and further functionalisations will be presented. Finally, preliminary results of a cooperative Frustrated Lewis Pair approach will be also discussed.

Item Type: Thesis (PhD)
Date Type: Completion
Status: Unpublished
Schools: Chemistry
Date of First Compliant Deposit: 21 November 2024
Last Modified: 22 Nov 2024 09:32
URI: https://orca.cardiff.ac.uk/id/eprint/174210

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