Organic Iodine Reagent-Catalyzed C-H Bond Functionalization

C-H bond functionalization has arisen as an excellent synthetic method because it reduces prefunctionalization while improving atom economy and energy efficiency.In spite of its prefect reactivity,the classical methods use of expensive metal catalysts and the problems involved in removing the residual metals from the final products,in which is usually a difficult and tedious process,limits the practical applications of this strategy.The discovery of an efficient C-H bond functionalization in the presence of organic iodine reagent would be of great value.The First chapter,we introduce the widely used organic iodine reagent PhI,TBAI catalytic C-H bond functionalization in detail.We also summarized the methods for synthesis of quinoxalines,?-carboxylic-?-ketoesters,allylic sulfones.The second chapter,quinoxaline derivatives were synthsized via one-pot two-steps process which using PhI/m-CPBA system to amination of C-H bond.As it report that iodobenzene as catalyst,m-CPBA as oxidant,in the presence of p-toluenesulfonic acid to construct Koser reagent.The reaction of acetophenone with Koser reagent generated a-tosyloxyl-ketones,followed by tandem nucleophilic substitution with o-phenylenediamines,dehydration cyclisation and dehydrogenation to construct quinoxalines.This reaction provides a good method for quinoxaline derivatives with low cost,easy operation and high yield.The third chapter,we have developed the Bu4NI/TBHP system to esterification of C-H bond.A catalytic amount of tetrabutylammonium iodide(TBAI),in the presence of tert-butyl hydroperoxide(TBHP),to form the corresponding hypervalent iodine reagents,hypervalent iodine reagents realized Cross-Dehydrogenative Coupling(CDC)of ?-ketoesters with carboxylic acid,to obtain 18 different ?-carboxy-?-ketoesters compound.The reaction is simple,mild conditions,and environmental friendliness.Finally,we have developed the Bu4NI/TBHP system to sulfonylation of C-H bond.TBHP decomposes to generate the tert-butoxyl and tert-butylperoxy radicals with the assistance of TBAI.These radicals subsequently abstract hydrogen atoms from sulfonylhydrazides to generate sulfonyl radicals.The addition of resultant sulfonyl radicals to alkenes affords sulfones.This strategy provides a good method for allylic sulfones with easy operation and environmental friendliness.The thesis aims at using organic iodine reagent PhI and TBAI catalytic C-H bond functionalization to synthesize quinoxalines,?-carboxylic-?-ketoesters,allylic sulfones.The reaction not only easily handled but also environmental friendliness.We also expand the use of organic iodine reagent.