KI catalyzed azidoselenenylation of alkenes with sodium azide and diselenides via an oxidative cleavage of Se–Se bond

GRAPHICAL ABSTRACT

ABSTRACT

Using potassium iodide as a catalyst and m-chloroperbenzoic acid as an oxidant, an efficient catalytic procedure has been developed for the azidoselenenylation of alkenes with sodium azide and diselenides, and a series of corresponding β-azidoselenides, most of which are new compounds, have been prepared in moderate to good yields under mild reaction conditions. This in situ generation of the electrophilic selenenylating reagents with addition to alkenes is a stereospecific anti addition, which occurs with a Markovnikov orientation.

KEYWORDS:

• Azidoselenenylation
• diselenide
• alkene
• sodium azide
• potassium iodide
• catalysis