Novel Green Chemical Reactions Development And Applications Involved With The Diaryliodonium Salts

This thesis mainly focused on the development of highly atom and step economical tanderm reactions involved with cyclic iodonium salts,and established diversified small molecule liabray which might lead to the discovery of lead compounds of telomerase inhibitor.This dissertation consists of three parts as following:In the first part,the methods about telomerase inhibitor design and synthesis were reviewed.Firstly the character and function of the telomere in cell were introduced.Secondly the mechanism of action about telomerase and telomerase’s inhibitor were introduced.Finally,different types of telomerase’s inhibitors were presented in detail.In the second part,highly selective and atom-economical copper catalyzed acid diphenylation method was developed.With readily available cyclic iodonium salts and various carboxylic acids as starting materials,a series of novel biphenylated esters with an extra iodine functional group were synthesised in a simple and efficient way.Compared with the method previously reported by Olofsson and co-workers,our methoud has more advantage,by which both the diphenylation and mono-arylation can be achieved.Furthermore,the carboxylic acid can be selectively arylated in the presence of phenolic amine,hydroxy and thiol groups.After the substrate scopes investigation,a series of novel and useful derivatives were obtained by further transformation of the biphenylated ester products,which demonstrated the utility and importance of this novel method.In the third part,a method for the synthesis of poly(hetero)aryl containing middle-sized lactones(potential telomerase inhibitors)were developed.Based on the diphenylation of carboxylic acids,a diphenylation/Sonogashira coupling one-pot cascade reaction was developed for the synthesis of functionalized biphenyl esters.Followed by tanderm azidation/metal free Click reaction,a series of novel poly(hetero)aryl containing middle-sized lactones were prepared for the first time.Currently,the biological activity screening of these small molecules is ongoing by collaborating with the other research groups.