Studies On The Gold Catalyzed Tandem Cyclization (Fluorination) Reactions

This thesis consists of four chapters. The first chapter reviews the applications of gold catalysts in organic synthesis; the second one focuses on AuCl3/AgOTf system-catalyzed tandem conjugate addition/annulation of4-hydroxycoumarins with α,β-unsaturated ketones; the third one deals with gold-catalyzed tandem cyclization of allene esters to synthesize fluoroindene derivatives; the last one is conclusion and outlook of gold catalysis.In the first chapter, first of all, we fully reviewed the physical and chemical properties of the metal gold, historical development and current situation of the application of gold catalysts in organic synthesis. On the basis of the above background, the main idea and designing of this thesis is discussed.The second chapter focuses on the AuCl3/AgOTf system-catalyzed tandem conjugate addition/annulation of4-hydroxycoumarins with α,β-unsaturated ketones to synthesize pyranocoumarins under mild conditions, and the reaction can get high yields, of which the highest is98%with excellent regioselectivity. The third chapter focuses on the gold-catalyzed three-component tandem reaction between allene esters, Selectfluor, and water to synthesize fluoroindene derivatives. It has been found that the gold-catalyzed transformation of allene esters displayed versatility and diversity in affording a diversity of product patterns merely via subtle structural variation of the allene esters. Compared with conventional methods for synthesis of fluoroindenes, the present method has advantages of high regioselectivity, mild reaction conditions, one-pot manner, readily accessible material.In the last chapter, we make a summary and prospected the application of gold catalysts in organic synthesis.