Selective Oxidation Of Sulfides And CuI Catalyzed C-C Coupling Reactions

This dissertation consists of four chapters. The first chapter, the oxidation of sulfides to sulfoxides is briefly reviewed. The second one is a review about coupling reactions with copper as catalyst. The third one is about the selective oxidation of sulfides to sulfoxides in the presence of an ionic liquid containing hypervalent iodine. CuI/L-proline-catalyzed coupling reaction of vinyl bromides with activated methylene compounds is studied in the fourth chapter.The chapter one is mainly about the oxidation of sulfides with various of oxidants, including molecular halogens, hypochloretes, chlorites and bromites, bromates, hypervalent iodine(III) reagents.The chapter two deals mainly with coupling reactions with copper as a catalyst. We discuss the reaction condition of this type coupling reaction and study the effects of ligands, solvents and bases on the results. In this chapter, we also give a brief summary about copper-catalyzed C-N, C-O, C-S and C-C coupling reactions.Selective oxidation of sulfides to sulfoxides is stutied in chapter three. We have developed a simple, mild, and environmentally benign method for the synthesis of sulfoxides by the oxidation of sulfides with hypervalent iodine reagent [dibmim]⁺[BF4]^-in water. This method offers the advantage of shorter reaction times, high chemoselectivity, and easy work up. The ion-supported hypervalent iodine reagent [dibmim]⁺[BF₄]^- is readily recovered and reused.In chapter four, CuI/L-proline-catalyzed coupling reaction of vinyl bromides with activated methylene compounds is described. The yields of these reactions are moderate to good. The products getting from this method bearing a variety of functional groups are very useful synthetic intermediates which can be readily for further reactions.