Application Of Ytterbium Reagent As Nucleophile Reagent And Single Electron Transfer Reagent In Synthesis Of 3-substituted-2-oxindoles

The thesis mainly includes the applications of ytterbium reagent as nucleophile reagent and single electron transfer reagent in the synthesis of 3-substituted-2-oxindoles.1.Study on the application of ytterbium reagent as nucleophile reagent in the synthesis of 3-hydroxy-3-alkyl-2-oxindoles.3-hydroxy-3-alkyl-2-oxindoles have potential biological activity and can be used as a key precursor in the synthesis of biologically active molecules and natural products,so they have attracted increasing attention.The first part of the article explores a new method to synthesize such compounds by Grignard reaction and Barbier reaction of ytterbium reagent with isatin.This method has the advantages of one-pot reaction,wide application range of reaction substrate,mild reaction conditions and high yield.2.Study on the application of ytterbium reagent as nucleophile reagent and single electron transfer reagent in the synthesis of 3-substituted-2-oxindoles.Although the divalent ytterbium Grignard reagent has been widely used in organic synthesis as a nucleophile reagent,it can be used as a single electron transfer reagent that has not been reported in the literature so far.The second part of the article investigated the single-electron transferability of the divalent ytterbium Grignard reagent for the first time:We found that with the promotion of diphenyl phosphite,in the Grignard reaction and Barbier reaction of ytterbium reagent and isatin,the ytterbium reagent was used both as a nucleophile reagent and a single electron transfer reagent.This is not only the first demonstration of the single-electron transferability of the divalent ytterbium Grignard reagent,but also a new and efficient method for the synthesis of 3-substituted-2-oxindoles.