Investication Of Transition-metal Free Esterification Reaction And Asymmetric Dearomatization Fluorination Of Naphthols

Esters are a class of important organic chemical intermediates and pharmaceutical intermediates,and exsit in many chemical products,food and pharmaceutical ingredients;and is of great value in our lives.In recent years,the synthesis of ester compounds has attracted more and more interest.Our thesis focuses on the synthesis of carboxylic acid esters by the oxidation of aldehydes and halogenated alkanes;and the asymmetric dearmoatization fluorination reaction of naphthols catalyzed by chiral phosphoric acid.The main contents of this thesis are as follows:In the first chapter,the synthetic history of ester compounds is introduced.There are many kinds of esters,which can be obtained from the reaction of carboxylic acid and alcohols.We herein reviewed the esterification reaction catalyzed with or without the transition metals from different starting materials.In the second chapter,the transition metal free esterification reaction of aldehydes and haloalkanes was described.In this chapter,the synthesis of ester compounds was carried out in the presence of tetrabutylammonium iodide under the catalysis of tetrabutylammonium iodide.The corresponding products could be obtained in good yields.The method has the advantages of simple operation,mild reaction conditions and good reaction characteristics.At last,the chiral phosphoric acid catalyzed asymmetric dearomatization fluorination of naphthols was developed.In this chapter,by using of chiral phosphoric acid catalyst under inorganic base conditions,a new type of chiral phase transfer catalyst could be generated,and applied in the asymmetric fluorination of naphthols.The fluorinated dearomatization produtcs were achied in excellent yields and moderate to good enantioselectivities;we also tried naphthol as asymmetric bromination and iodination reactions un der identical conditions.