Studies On The Catalytic Application Of Inorganic Iodides For The Acetoxyseleneylation And Selenolactonization Of Alkenes

In this dissertation,we have studied on the catalytic acetoxyseleneylation and selenolactonization of alkenes using inorganic iodides as catalysts.This dissertation mainly includes three parts:1.Review.This chapter introduces the history and progress of organic selenium reagents,especially focus on their reactions in organic synthesis and the main reaction mechanisms.2.The acetoxyseleneylation of alkenes catalyzed by inorganic iodides.With inorganic iodides as catalysts and m-chloroperbenzoic acid as the oxidant,a novel and efficient catalytic procedure has been developed for the acetoxyselenenylation of alkenes.In this protocol,inorganic iodine is first oxidized into hypoiodite,which rapidly reacts with diselenide to form the active electrophilic selenenylating reagent,following an electrophilic addition of alkenes.This catalytic reaction is different from those of using stoichiometric equivalent hypervalent iodine reagents.In the meanwhile,using inorganic chloride or inorganic bromide instead of inorganic iodide,it is found that the similar reaction can be also carried out fluently,resulting in the formation of the corresponding acetoxyselenides in good yields.3.The selenolactonization of unsaturated carboxylic acids catalyzed by inorganic iodides.A mild method for the selenolactonization of unsaturated carboxylic acids has been developed with diselenide and a catalytic amount of inorganic iodide in the presence of mCPBA at room temperature.This method is very simple and regioselectivity.It also gives good results in the tellurolactonization of the same substrate.