Iron(III)-catalyzed aerobic dioxygenation of styrenes using N-hydroxyphthalimide and N-hydroxybenzotriazole

Abstract

Iron-catalyzed dioxygenation of alkenes in air using N-hydroxyphthalimide (NHPI) and N-hydroxybenzotriazole (HOBt) is described at room temperature. The products can be readily converted into 1,2-vicinal diols using PPh₃ and Mo(CO)₆. The use of Fe(NO₃)₃·9H₂O as the catalyst, mild reaction conditions and the selectivity are the significant practical features. The radical scavenger experiment suggests that the reaction proceeds via a radical intermediate. The synthetic and mechanistic aspects have been presented.