Synthesis, study and application of NHC-gold(I) complexes
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The development of procedures for the synthesis of valuable organic molecules constitutes an important part of chemistry. The goal of improving the efficiency of existing methodologies can be fulfilled by use of metal catalysts. Recent developments in the field of homogeneous gold catalysis have contributed to these efforts and continued investigations assure future innovations. Chapter 1 summarises the properties of gold and ligand-supported gold(I) complexes and demonstrates how a detailed understanding of its reactivity and possible bonding interactions with various substrates facilitates the development of well-defined catalytic systems. Particular attention is given to N-heterocyclic carbenes, highly tunable ligands that stabilise a wide range of different transition metal complexes. Three chapters describe syntheses and studies of known and new complexes. Chapter 2 discusses expedient syntheses of key NHC-gold(I) complexes and catalysts. Chapter 3 constitutes studies to the behaviours of the commonly used tetrafluoroborate counterion in a particular IPr¬¬¬¬CI¬-gold(I) complex. Chapter 4 describes the synthesis of a range of IPr-gold(I) carbanion complexes form the widely studied IPr-gold(I) hydroxide synton, the study of their properties and exploration of their reactivity. Catalytic applications in transformations of alkynes and alcohols are described in the last three chapters. Chapter 4 details the development of efficient NHC-gold(I)-catalysed procedures for the synthesis of vinyl ethers through addition reactions of aliphatic and benzylic alcohols. Appendix A describes preliminary explorations to the complimentary use of Brønsted acidic compounds as catalysts for the formation of products with new C-C bonds from benzylic alcohols and phenols
Thesis, PhD Doctor of Philosophy
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