Study On Electrochemical Oxidation Preparation Of Selenium Substituted Iminobenzoisofuran And Glycosyl Disulfides

Through rapid development in recent years,electrochemical synthesis has played an increasingly important role in organic synthesis.Compared to traditional organic synthesis,it is a more green and environmentally friendly organic synthesis method.Due to the inevitable use of stoichiometric oxidants or reducing agents in traditional synthesis steps,a large amount of waste is inevitably generated,causing significant harm to the environment.As an efficient and mild synthesis tool,electrosynthesis can undergo oxidation reactions at the anode and reduction reactions at the cathode through electron transfer without the need for additional oxidants and reducing agents.The substrate undergoes a single electron transfer process on the electrode surface through anodic oxidation,producing highly active free radical species.After that,the next step of transformation can easily form C-E bonds(E = C,N,S,Se,O,P,and X,etc.).This paper successfully achieved the following two tasks through electrochemical oxidation:1.Selenium free radicals are generated by electrochemical oxidation of diselenides,and then a series of free radical cyclization reactions are carried out on the substrate enamide with unsaturated double bonds,resulting in the formation of five membered heterocyclic selenium substituted iminobenzofuran.This reaction can be compatible with various site substituted enamides,and compared to the traditional synthesis method of iminobenzofuran,it does not require the use of additional oxidants and additives,and has the advantage of being clean and environmentally friendly.The proposed reaction mechanism was further demonstrated through free radical capture experiments and cyclic voltammetry experiments.2.Through the electrochemical oxidation dehydrogenation coupling strategy,the S-S bond is formed by oxidizing the glycosyl thiol SH with another molecule of thiol SH in an undivided cell,generating glycosyl disulfides.During the reaction,the proton will release valuable hydrogen at the cathode.Oxidize rich electron aromatic hydrocarbons CH and glycosyl thiols SH,construct C-S bonds,and generate rich electron aromatic glucosinolate.This strategy does not require pre-functionalized glycosyl sulfides or oxidants to generate asymmetric glycosyl disulfides and glucosinolate.Reactions can construct various asymmetric glycosyl disulfides,and different types of glycosyl thiols can smoothly couple with cysteine.