DEVELOPMENT OF SILVER CATALYSTS FOR THE HETEROCYCLIZATION REACTIONS OF ALKYNES

WONG HUI LIN VALERIE

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DEVELOPMENT OF SILVER CATALYSTS FOR THE HETEROCYCLIZATION REACTIONS OF ALKYNES

WONG HUI LIN VALERIE

Abstract

This PhD thesis describes work undertaken to develop efficient silver(I) catalysts for the intramolecular reactions of alkynes with nitrogen and oxygen containing nucleophiles for the synthesis of heterocycles. The introductory chapter provides an overview of recent advances in silver-catalyzed heterofunctionalization reactions of alkynes, with a focus on reactions involving C-N and C-O bond formations. Chapter 2 describes the screening of silver salts as catalysts for the intramolecular hydroamination of alkynes with trichloroacetimidates. In Chapter 3, the application of the pyridine-ligated silver salts developed in Chapter 2 as catalysts for the cycloisomerization of propargyl amides is described. In Chapter 4, the synthesis and characterization of a new class of silver(I) NHC carboxylate complexes are presented. The activity towards the cycloisomerization of propargyl amides was investigated, and they showed complementary reactivities compared to the pyridine-ligated silver catalysts in Chapter 3. In Chapter 5, an overall conclusion and future work are discussed. The last Chapter contains experimental procedures and characterization data of all the compounds synthesized during the course of this project.