Disulfoxides Synthesis And Disulfoxides-Palladium Catalyzed Allylic C-H Bond Activation

Sulfoxide compounds are a kind of important intermediates,having a wide range of applications in chemical, biological and many industries. Sulfoxide compounds can also be served as the ligand,cooperating with transition metal,and used in asymmetric catalytic reactions, C - H activation reaction, etc.Transition metal catalysis has long been regarded as one of the most effective method of forming chemical bonds, and has become a very powerful tool of building C-X bond.Compared with traditional ligands,sulfoxides can be obtained by simple and effective method. Being used as catalyst in the functionalization of the allylic C-H bond of alkenes is one of its most successful applications for the disulfoxide ligand. However,the present work focused on only a handful of several pairs of sulfoxide ligands. We designed and synthesized a series of disulfoxide to expand the ligand library, making it get more extensive application.At first, we design and synthesis 18 kinds of disulfoxides (most of them had not been reported), then those ligand was tested to found better catalytic properties in the functionalization of the allylic C-H bond of alkenes(building C-O bond, C-C bond). On the one hand, we study the influence of the ligands's structure on the reaction , On the other hand,screen out disulfoxide ligands with better catalytic properties for further application. We have got an good result(the yield is 78%) when dicarbonyl compounds was used as nucleophilic substances,1,2-bis(dibenzyl)ethane sulfoxide/Palladium acetate as catalyst to bulid C-C bond, this result is comparable with literature reported. When acetic acid or benzoic acid was used as nucleophilic reagent, 1,2-bis(cyclohexyl)ethane sulfoxide/Palladium acetate as catalyst, we have got very high yield (99%). And almost all branched chain products.Then 1,2-bis(cyclohexyl)ethane sulfoxide was further applied to allyl esterification and three components coupling of alkenes, aromatic carboxylic acid and boric acid, giving 13 kinds of structural complexed valuable compounds.