Transition Metal-catalyzed Oxidation Of C=C Bonds

Catalytic oxidation is a very important transformation of the readily available petroleum-based feed-stocks into useful high oxidation state chemicals such as alcohols and carbonyl compounds.In addition,the process of catalytic oxidation plays a key role in chemical agrochemicals,pharmaceuticals,science materials and large-scale commodities.In this regarding,the C=C double bonds are amongst the most fundamental groups in organic molecules,the formation of carbonyl containing building blocks or active molecules through the oxidation of C=C bonds is of high interest in organic synthesis and drug discovery.Acetophenones and isatins are important building blocks for organic synthesis,acetophenones are widely used in soap make,plastification,essence allocation.while,isatins are important motifs in many natural products and drug molecule.In the thesis,the transition-metal-catalyzed oxidation of styrenes and indoles into the corresponding acetophenones and isatins will be describle.Three sections will be included:1)The-state-of-the-art of the transition-metal-catalyzed oxidation will be summarized in this section,and mainly Pd-and Cu-catalyzed oxidation by the use of oxygen,hydrogen peroxide,tert-butyl hydroperoxide as oxidants will be discussed.2)A convenient protocol for the oxidation of an alkene to the corresponding ketone was developed.This method allows Wacker-type oxidation to undergo efficiently at room temperature in the presence of a commercial available palladium catalyst and cheap aqueous tert-butyl peroxide without the requirement of an extra additive or ligand.This transformation is highly functional groups tolerant,and aliphatic alkenes,di-substituted alkenes and intertnal alkenes could also be converted into ketones.3)The first example of Cu-catalyzed oxidation of indole derivatives to Isatins by the use of cheap aqueous tert-butyl peroxide as an oxidant was developed.This oxidation reaction is practically convenient and highly functional group tolerant,and proceeds under relatively mild conditions without the addition of any additive or ligand.Mechanistic studies suggest that the two oxygen atoms of the isatins products mainly originate from water.