A Novel and Efficient Alkoxylselenenylation of Alkenes

A novel and efficient alkoxylselenenylation from alkenes, diselenides, and alcohols mediated by iodine is developed, with which a series of β-alkoxy selenides are synthesized. In this procedure, firstly, I2 reacts with diselenide to form in situ the active electrophilic selenium species RSeI, then following an electrophilic addition of it to alkenes provides β-alkoxy selenides with high regioselectivity and in good yields. This new method for achieving β-alkoxy selenides has some advantages over other methods such as using available and cheap iodine as the oxidizing species at room temperature, which makes this reaction has milder reaction conditions and simpler procedure.

Yingguo Fang and Jie Yan