The development of new synthetic strategies using lewis acidic boron and iron catalysts

Elsherbeni, Salma 2024. The development of new synthetic strategies using lewis acidic boron and iron catalysts. PhD Thesis, Cardiff University. Item availability restricted.

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Abstract

This thesis describes the development of new organic transformations facilitated by Lewis acidic boron and iron catalysts. The research is driven by the need to develop greener alternatives to traditional precious metal-catalyzed reactions, focusing on the synthesis and functionalization of complex organic molecules. Chapter 1 provides an overview of Lewis acidity, highlighting the fundamental principles and catalytic applications of Lewis acidic boranes and iron complexes. Key transformations such as hydride abstraction, C-H functionalization, and transfer hydrogenation are discussed, emphasizing the versatility and efficiency of these catalysts. Chapter 2 discusses the synthesis and applications of (cyclopentadienone)iron carbonyl complexes in transfer hydrogenation and borrowing hydrogen reactions. The chapter also presents the development of a simple and efficient protocol for the ironcatalyzed transfer hydrogenation of allylic alcohols using isopropanol as the hydrogen donor. Utilizing a well-defined (cyclopentadienone)iron carbonyl complex as a precatalyst in combination with K2CO3, the method achieves high yields for a diverse range of allylic alcohols. The scope and limitations of the reaction are explored, and mechanistic studies provide insights into the catalytic cycle. Chapter 3 investigates two B(C6F5)3-catalyzed methodologies: secondary alkyl group transfer and E-selective isomerization of allylic substrates. The first section describes the successful alkylation of indoles using various secondary alkyl group donors, highlighting the optimization of reaction conditions, substrate scope, and mechanistic studies. The second section focuses on the isomerization of 1-alkenes to 2-alkenes, detailing the reaction optimization and mechanistic insights. The chapter showcases the versatility of B(C6F5)3 in mediating different types of reactions, contributing to the development of new synthetic methodologies for complex organic molecules.

Item Type:	Thesis (PhD)
Date Type:	Completion
Status:	Unpublished
Schools:	Chemistry
Date of First Compliant Deposit:	29 October 2024
Last Modified:	29 Oct 2024 09:39
URI:	https://orca.cardiff.ac.uk/id/eprint/173494

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