Novel and convenient acetoxyselenenylation of alkenes catalyzed by potassium iodide

•We find a novel catalytic procedure of inorganic iodides for acetoxyselenenylation of alkenes.•The catalytic reaction conditions of KI are optimized.•A series of 2-acetoxy-1-selenenylation compounds, most are new compounds are prepared.•A plausible mechanism is suggested.

With KI as catalyst and m-chloroperbenzoic acid as the oxidant in acetic acid, a novel and efficient catalytic procedure has been developed for acetoxyselenenylation of alkenes, which providing a series of 2-acetoxy-1-selenenylation compounds with high regioselectivity and good yields in mild conditions. In this protocol, KI is first oxidized by m-chloroperbenzoic acid into acetylhypoiodite, which rapidly reacts with diselenide to form the active electrophilic selenenylating reagent, following an electrophilic addition of alkenes and 2-acetoxy-1-selenenylation compounds are obtained. The suitable equivalent ratio of alkene to diselenide is 1.2.

Graphical abstractWith KI as catalyst, a novel and efficient catalytic procedure has been developed for acetoxyselenenylation of alkenes, which providing a series of 2-acetoxy-1-selenenylation compounds with high regioselectivity and good yields in mild conditions.Figure optionsDownload full-size imageDownload as PowerPoint slide