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With PhI as catalyst and mCPBA as oxidant, a novel and efficient catalytic procedure has been developed for the acetoxyselenylation and formyloxyselenylation of alkenes. In this protocol, PhI is first oxidized into hypervalent iodine intermediate, which promotes the cleavage of Se-Se bond in diselenides. The in situ generated electrophilic selenium species then reacts with alkenes, affording 2-acetoxy-1-selenides and 2-formyloxy-1-selenides in high regioselectivity and good yields. [ABSTRACT FROM AUTHOR]

In the presence of NH4I as catalyst and m-chloroperbenzoic acid as oxidant, the Se-Se bond cleavage of diselenides undergoes smoothly. The in situ generated reactive electrophilic Se species reacts with alkenes quickly, and a series of β-hydroxy selenides are prepared in good yields. This new catalytic method for synthesis of β-hydroxy selenides is a stereospecific anti addition, which occurs with a Markovnikov orientation. [ABSTRACT FROM AUTHOR]