Study On The Synthesis Of S-N Bonds Under Electrochemical Conditions

Sulfenamides,a class of organosulfur compounds containing sulfur nitrogen bonds,have attracted significant attention in various fields due to their important applications in organic synthesis,light state therapy,material chemistry,food science,especially in pharmaceutical.Traditional methods for the synthesis of such compounds usually require transition metal catalysis and the participation of chemical quantities of organic oxidants,and the reactions proceed while also producing chemical quantities of byproducts,which do not conform to the concept of green chemistry development.In contrast,electrochemical catalysis,as a green synthetic method,has become a research hotspot in the field of organic synthesis in recent years.Therefore,a green nonfouling and efficient electrochemical method for the preparation of sulfenamides was developed.Direct synthesis of sulfenamides from thiophenols(or thiols)and secondary amines coupled by electrochemical oxidation is presented in this paper.This method,using ki as the electrolyte,takes advantage of the working principle of the electrolysis cell,i.e.,both gain and loss of electrons,to carry out the reaction and avoid the use of oxidants.A study of the universality of the reaction revealed that both thiophenols(or thiols)and secondary amines could proceed under optimal conditions,and sulfenamides were obtained in moderately to superior yields.The reaction also underwent gram scale preparation,which provides good prospects for industrial production.The reaction was deduced to be a radical reaction by controlling the experimental and mechanistic investigations.